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[ CAS No. 133498-97-2 ] {[proInfo.proName]}

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Chemical Structure| 133498-97-2
Chemical Structure| 133498-97-2
Structure of 133498-97-2 * Storage: {[proInfo.prStorage]}
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Quality Control of [ 133498-97-2 ]

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Product Details of [ 133498-97-2 ]

CAS No. :133498-97-2 MDL No. :MFCD24465606
Formula : C10H18N2O5 Boiling Point : -
Linear Structure Formula :- InChI Key :VNYXZTSJRJLBSO-UHFFFAOYSA-N
M.W : 246.26 Pubchem ID :10977741
Synonyms :

Calculated chemistry of [ 133498-97-2 ]

Physicochemical Properties

Num. heavy atoms : 17
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.7
Num. rotatable bonds : 8
Num. H-bond acceptors : 5.0
Num. H-bond donors : 2.0
Molar Refractivity : 59.57
TPSA : 95.94 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.77 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.68
Log Po/w (XLOGP3) : 0.05
Log Po/w (WLOGP) : 0.05
Log Po/w (MLOGP) : -0.17
Log Po/w (SILICOS-IT) : -0.71
Consensus Log Po/w : 0.18

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -0.87
Solubility : 33.2 mg/ml ; 0.135 mol/l
Class : Very soluble
Log S (Ali) : -1.62
Solubility : 5.94 mg/ml ; 0.0241 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.69
Solubility : 49.8 mg/ml ; 0.202 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 2.37

Safety of [ 133498-97-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 133498-97-2 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 133498-97-2 ]

[ 133498-97-2 ] Synthesis Path-Downstream   1~50

  • 3
  • [ 174311-10-5 ]
  • [ 133498-97-2 ]
YieldReaction ConditionsOperation in experiment
100% With lithium hydroxide
100% With lithium hydroxide In tetrahydrofuran; methanol; water at 25℃; for 3h;
  • 4
  • [ 133498-97-2 ]
  • [ 89536-89-0 ]
  • [ 174311-12-7 ]
YieldReaction ConditionsOperation in experiment
85% With dmap; triethylamine; dicyclohexyl-carbodiimide In dichloromethane at 25℃; for 24h;
  • 5
  • [ 220883-24-9 ]
  • [ 133498-97-2 ]
  • [ 220883-25-0 ]
YieldReaction ConditionsOperation in experiment
83% With 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 23℃;
With 2,6-dimethylpyridine; 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane; N,N-dimethyl-formamide at 25℃; for 24h;
  • 6
  • [ 133498-97-2 ]
  • N-Me-Leu-OBzl p-toluenesulfonic acid salt [ No CAS ]
  • [ 133525-56-1 ]
YieldReaction ConditionsOperation in experiment
With 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 20h;
  • 7
  • [ 4530-20-5 ]
  • [ 133498-97-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1-hydroxybenzotriazole hydrate; N-(3-dimethyaminopropyl)-N'-ethylcarbodiimide hydrochloride; diisopropylethylamine / dimethylformamide / 20 h 2: hydrogen / Pd/C / ethyl acetate / 16 h
  • 8
  • [ 133498-97-2 ]
  • H-Gly-sarcosyl-ψ(CONCH3)Leu-OH trifluoroacetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 1-hydroxybenzotriazole hydrate; N-(3-dimethyaminopropyl)-N'-ethylcarbodiimide hydrochloride; diisopropylethylamine / dimethylformamide / 20 h 2: hydrogen / Pd/C / ethyl acetate / 16 h 3: CH2Cl2 / 3 h
  • 9
  • [ 133498-97-2 ]
  • [ 133499-00-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1-hydroxybenzotriazole hydrate; N-(3-dimethyaminopropyl)-N'-ethylcarbodiimide hydrochloride; diisopropylethylamine / dimethylformamide / 20 h 2: hydrogen / Pd/C / ethyl acetate / 16 h
Multi-step reaction with 2 steps 1: 1.) Et(i-Pr)2N, BOP-Cl; 2.) Et(i-Pr)2N / CH2Cl2; 1.) -18 deg C, 90 min; 2.) room temp., overnight 2: 99 percent / hydrogen / 10percent Pd/C / ethanol / 15 h
  • 10
  • [ 4530-20-5 ]
  • [ 133498-97-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 80 percent / Et3N, DCC, DMAP / CH2Cl2 / 20 h / 25 °C 2: 100 percent / LiOH*H2O / tetrahydrofuran; methanol; H2O / 3 h / 25 °C
Multi-step reaction with 2 steps 1: dicyclohexylcarbodiimide, 1-hydroxybenzotriazole 2: H2 / 10percent Pd/charcoal
Multi-step reaction with 2 steps 1: 1.) Et3N, ethyl chloroformate; 2.) Et3N / toluene, CHCl3; 1.) -17 deg C, 20 min; 2.) 50 deg C, 30 min 2: 99 percent / hydrogen / 10percent Pd/C / ethanol / 18 h / Ambient temperature
  • 11
  • [ 133498-97-2 ]
  • [ 151961-26-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: 74 percent / Et3N, DCC, DMAP / CH2Cl2 / 24 h / 25 °C 2: 90 percent / LiOH*H2O / tetrahydrofuran; methanol; H2O / 3 h / 25 °C 3: 50 percent / DMAP, DCC / CH2Cl2 / 24 h / 0 °C 4: H2 / 10percent Pd/C / methanol / 12 h / 25 °C 5: 80 percent / NaHCO3, HOBt, EDCl / dimethylformamide / a) 0 deg C, 2 h, b) 25 deg C, 24 h 6: 97 percent / H2 / 10percent Pd/C / methanol / 16 h / 760 Torr
Multi-step reaction with 6 steps 1: 74 percent / Et3N, DCC, DMAP / CH2Cl2 / 24 h / 25 °C 2: 90 percent / LiOH*H2O / tetrahydrofuran; methanol; H2O / 3 h / 25 °C 3: 50 percent / DMAP, DCC / CH2Cl2 / 24 h / 0 °C 4: 3M HCl / ethyl acetate / 0.5 h / 25 °C 5: 80 percent / NaHCO3, HOBt, EDCl / dimethylformamide / a) 0 deg C, 2 h, b) 25 deg C, 24 h 6: 97 percent / H2 / 10percent Pd/C / methanol / 16 h / 760 Torr
Multi-step reaction with 6 steps 1: 85 percent / Et3N, DMAP, DCC / CH2Cl2 / 24 h / 25 °C 2: H2 / 10percent Pd/C / methanol / 16 h / 25 °C / 760 Torr 3: 50 percent / DMAP, DCC / CH2Cl2 / 24 h / 0 °C 4: H2 / 10percent Pd/C / methanol / 12 h / 25 °C 5: 80 percent / NaHCO3, HOBt, EDCl / dimethylformamide / a) 0 deg C, 2 h, b) 25 deg C, 24 h 6: 97 percent / H2 / 10percent Pd/C / methanol / 16 h / 760 Torr
Multi-step reaction with 6 steps 1: 85 percent / Et3N, DMAP, DCC / CH2Cl2 / 24 h / 25 °C 2: H2 / 10percent Pd/C / methanol / 16 h / 25 °C / 760 Torr 3: 50 percent / DMAP, DCC / CH2Cl2 / 24 h / 0 °C 4: 3M HCl / ethyl acetate / 0.5 h / 25 °C 5: 80 percent / NaHCO3, HOBt, EDCl / dimethylformamide / a) 0 deg C, 2 h, b) 25 deg C, 24 h 6: 97 percent / H2 / 10percent Pd/C / methanol / 16 h / 760 Torr
Multi-step reaction with 6 steps 1: 74 percent / DCC, Et3N, DMAP / CH2Cl2 / 24 h / 25 °C 2: 90 percent / aq. LiOH / tetrahydrofuran; methanol / 3 h / 25 °C 3: 71 percent / DCC, DMAP / CH2Cl2 / 24 h / 0 °C 4: 98 percent / H2 / 10percent Pd/C / methanol / 12 h / 25 °C 5: 81 percent / EDCI, HOBt, NaHCO3 / CH2Cl2 / 24 h / 25 °C 6: H2 / 10percent Pd/C / methanol / 12 h / 25 °C
Multi-step reaction with 6 steps 1: 74 percent / DCC, Et3N, DMAP / CH2Cl2 / 24 h / 25 °C 2: 90 percent / aq. LiOH / tetrahydrofuran; methanol / 3 h / 25 °C 3: 71 percent / DCC, DMAP / CH2Cl2 / 24 h / 0 °C 4: 100 percent / 3 M HCl / ethyl acetate / 0.5 h / 25 °C 5: 81 percent / EDCI, HOBt, NaHCO3 / CH2Cl2 / 24 h / 25 °C 6: H2 / 10percent Pd/C / methanol / 12 h / 25 °C

  • 12
  • [ 133498-97-2 ]
  • [ 151961-25-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 74 percent / Et3N, DCC, DMAP / CH2Cl2 / 24 h / 25 °C 2: 90 percent / LiOH*H2O / tetrahydrofuran; methanol; H2O / 3 h / 25 °C 3: 50 percent / DMAP, DCC / CH2Cl2 / 24 h / 0 °C 4: H2 / 10percent Pd/C / methanol / 12 h / 25 °C 5: 80 percent / NaHCO3, HOBt, EDCl / dimethylformamide / a) 0 deg C, 2 h, b) 25 deg C, 24 h
Multi-step reaction with 5 steps 1: 74 percent / Et3N, DCC, DMAP / CH2Cl2 / 24 h / 25 °C 2: 90 percent / LiOH*H2O / tetrahydrofuran; methanol; H2O / 3 h / 25 °C 3: 50 percent / DMAP, DCC / CH2Cl2 / 24 h / 0 °C 4: 3M HCl / ethyl acetate / 0.5 h / 25 °C 5: 80 percent / NaHCO3, HOBt, EDCl / dimethylformamide / a) 0 deg C, 2 h, b) 25 deg C, 24 h
Multi-step reaction with 5 steps 1: 85 percent / Et3N, DMAP, DCC / CH2Cl2 / 24 h / 25 °C 2: H2 / 10percent Pd/C / methanol / 16 h / 25 °C / 760 Torr 3: 50 percent / DMAP, DCC / CH2Cl2 / 24 h / 0 °C 4: H2 / 10percent Pd/C / methanol / 12 h / 25 °C 5: 80 percent / NaHCO3, HOBt, EDCl / dimethylformamide / a) 0 deg C, 2 h, b) 25 deg C, 24 h
Multi-step reaction with 5 steps 1: 85 percent / Et3N, DMAP, DCC / CH2Cl2 / 24 h / 25 °C 2: H2 / 10percent Pd/C / methanol / 16 h / 25 °C / 760 Torr 3: 50 percent / DMAP, DCC / CH2Cl2 / 24 h / 0 °C 4: 3M HCl / ethyl acetate / 0.5 h / 25 °C 5: 80 percent / NaHCO3, HOBt, EDCl / dimethylformamide / a) 0 deg C, 2 h, b) 25 deg C, 24 h
Multi-step reaction with 5 steps 1: 74 percent / DCC, Et3N, DMAP / CH2Cl2 / 24 h / 25 °C 2: 90 percent / aq. LiOH / tetrahydrofuran; methanol / 3 h / 25 °C 3: 71 percent / DCC, DMAP / CH2Cl2 / 24 h / 0 °C 4: 98 percent / H2 / 10percent Pd/C / methanol / 12 h / 25 °C 5: 81 percent / EDCI, HOBt, NaHCO3 / CH2Cl2 / 24 h / 25 °C
Multi-step reaction with 5 steps 1: 74 percent / DCC, Et3N, DMAP / CH2Cl2 / 24 h / 25 °C 2: 90 percent / aq. LiOH / tetrahydrofuran; methanol / 3 h / 25 °C 3: 71 percent / DCC, DMAP / CH2Cl2 / 24 h / 0 °C 4: 100 percent / 3 M HCl / ethyl acetate / 0.5 h / 25 °C 5: 81 percent / EDCI, HOBt, NaHCO3 / CH2Cl2 / 24 h / 25 °C

  • 13
  • [ 133498-97-2 ]
  • C50H92N10O17S2Si2*ClH [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: 74 percent / Et3N, DCC, DMAP / CH2Cl2 / 24 h / 25 °C 2: 90 percent / LiOH*H2O / tetrahydrofuran; methanol; H2O / 3 h / 25 °C 3: 50 percent / DMAP, DCC / CH2Cl2 / 24 h / 0 °C 4: H2 / 10percent Pd/C / methanol / 12 h / 25 °C 5: 80 percent / NaHCO3, HOBt, EDCl / dimethylformamide / a) 0 deg C, 2 h, b) 25 deg C, 24 h 6: 97 percent / H2 / 10percent Pd/C / methanol / 16 h / 760 Torr 7: 100 percent / 3M HCl / ethyl acetate / 0.5 h / 25 °C
Multi-step reaction with 7 steps 1: 74 percent / Et3N, DCC, DMAP / CH2Cl2 / 24 h / 25 °C 2: 90 percent / LiOH*H2O / tetrahydrofuran; methanol; H2O / 3 h / 25 °C 3: 50 percent / DMAP, DCC / CH2Cl2 / 24 h / 0 °C 4: 3M HCl / ethyl acetate / 0.5 h / 25 °C 5: 80 percent / NaHCO3, HOBt, EDCl / dimethylformamide / a) 0 deg C, 2 h, b) 25 deg C, 24 h 6: 97 percent / H2 / 10percent Pd/C / methanol / 16 h / 760 Torr 7: 100 percent / 3M HCl / ethyl acetate / 0.5 h / 25 °C
Multi-step reaction with 7 steps 1: 85 percent / Et3N, DMAP, DCC / CH2Cl2 / 24 h / 25 °C 2: H2 / 10percent Pd/C / methanol / 16 h / 25 °C / 760 Torr 3: 50 percent / DMAP, DCC / CH2Cl2 / 24 h / 0 °C 4: H2 / 10percent Pd/C / methanol / 12 h / 25 °C 5: 80 percent / NaHCO3, HOBt, EDCl / dimethylformamide / a) 0 deg C, 2 h, b) 25 deg C, 24 h 6: 97 percent / H2 / 10percent Pd/C / methanol / 16 h / 760 Torr 7: 100 percent / 3M HCl / ethyl acetate / 0.5 h / 25 °C
Multi-step reaction with 7 steps 1: 85 percent / Et3N, DMAP, DCC / CH2Cl2 / 24 h / 25 °C 2: H2 / 10percent Pd/C / methanol / 16 h / 25 °C / 760 Torr 3: 50 percent / DMAP, DCC / CH2Cl2 / 24 h / 0 °C 4: 3M HCl / ethyl acetate / 0.5 h / 25 °C 5: 80 percent / NaHCO3, HOBt, EDCl / dimethylformamide / a) 0 deg C, 2 h, b) 25 deg C, 24 h 6: 97 percent / H2 / 10percent Pd/C / methanol / 16 h / 760 Torr 7: 100 percent / 3M HCl / ethyl acetate / 0.5 h / 25 °C
Multi-step reaction with 7 steps 1: 74 percent / DCC, Et3N, DMAP / CH2Cl2 / 24 h / 25 °C 2: 90 percent / aq. LiOH / tetrahydrofuran; methanol / 3 h / 25 °C 3: 71 percent / DCC, DMAP / CH2Cl2 / 24 h / 0 °C 4: 98 percent / H2 / 10percent Pd/C / methanol / 12 h / 25 °C 5: 81 percent / EDCI, HOBt, NaHCO3 / CH2Cl2 / 24 h / 25 °C 6: H2 / 10percent Pd/C / methanol / 12 h / 25 °C 7: 3 M HCl / ethyl acetate / 0.5 h / 25 °C
Multi-step reaction with 7 steps 1: 74 percent / DCC, Et3N, DMAP / CH2Cl2 / 24 h / 25 °C 2: 90 percent / aq. LiOH / tetrahydrofuran; methanol / 3 h / 25 °C 3: 71 percent / DCC, DMAP / CH2Cl2 / 24 h / 0 °C 4: 100 percent / 3 M HCl / ethyl acetate / 0.5 h / 25 °C 5: 81 percent / EDCI, HOBt, NaHCO3 / CH2Cl2 / 24 h / 25 °C 6: H2 / 10percent Pd/C / methanol / 12 h / 25 °C 7: 3 M HCl / ethyl acetate / 0.5 h / 25 °C

  • 14
  • [ 133498-97-2 ]
  • [ 151961-21-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 74 percent / Et3N, DCC, DMAP / CH2Cl2 / 24 h / 25 °C 2: 90 percent / LiOH*H2O / tetrahydrofuran; methanol; H2O / 3 h / 25 °C
Multi-step reaction with 2 steps 1: 85 percent / Et3N, DMAP, DCC / CH2Cl2 / 24 h / 25 °C 2: H2 / 10percent Pd/C / methanol / 16 h / 25 °C / 760 Torr
Multi-step reaction with 2 steps 1: 74 percent / DCC, Et3N, DMAP / CH2Cl2 / 24 h / 25 °C 2: 90 percent / aq. LiOH / tetrahydrofuran; methanol / 3 h / 25 °C
  • 15
  • [ 133498-97-2 ]
  • [ 151961-24-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 74 percent / Et3N, DCC, DMAP / CH2Cl2 / 24 h / 25 °C 2: 90 percent / LiOH*H2O / tetrahydrofuran; methanol; H2O / 3 h / 25 °C 3: 50 percent / DMAP, DCC / CH2Cl2 / 24 h / 0 °C 4: H2 / 10percent Pd/C / methanol / 12 h / 25 °C
Multi-step reaction with 4 steps 1: 85 percent / Et3N, DMAP, DCC / CH2Cl2 / 24 h / 25 °C 2: H2 / 10percent Pd/C / methanol / 16 h / 25 °C / 760 Torr 3: 50 percent / DMAP, DCC / CH2Cl2 / 24 h / 0 °C 4: H2 / 10percent Pd/C / methanol / 12 h / 25 °C
Multi-step reaction with 4 steps 1: 74 percent / DCC, Et3N, DMAP / CH2Cl2 / 24 h / 25 °C 2: 90 percent / aq. LiOH / tetrahydrofuran; methanol / 3 h / 25 °C 3: 71 percent / DCC, DMAP / CH2Cl2 / 24 h / 0 °C 4: 98 percent / H2 / 10percent Pd/C / methanol / 12 h / 25 °C
  • 16
  • [ 133498-97-2 ]
  • [ 151961-22-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 74 percent / Et3N, DCC, DMAP / CH2Cl2 / 24 h / 25 °C 2: 90 percent / LiOH*H2O / tetrahydrofuran; methanol; H2O / 3 h / 25 °C 3: 50 percent / DMAP, DCC / CH2Cl2 / 24 h / 0 °C
Multi-step reaction with 3 steps 1: 85 percent / Et3N, DMAP, DCC / CH2Cl2 / 24 h / 25 °C 2: H2 / 10percent Pd/C / methanol / 16 h / 25 °C / 760 Torr 3: 50 percent / DMAP, DCC / CH2Cl2 / 24 h / 0 °C
Multi-step reaction with 3 steps 1: 74 percent / DCC, Et3N, DMAP / CH2Cl2 / 24 h / 25 °C 2: 90 percent / aq. LiOH / tetrahydrofuran; methanol / 3 h / 25 °C 3: 71 percent / DCC, DMAP / CH2Cl2 / 24 h / 0 °C
  • 17
  • [ 133498-97-2 ]
  • (S)-1-[(R)-3-[(S)-2-({2-[(2-Amino-acetyl)-methyl-amino]-acetyl}-methyl-amino)-3-methyl-butyryloxy]-2-(2-trimethylsilanyl-ethanesulfonylamino)-propionyl]-piperidine-2-carboxylic acid benzyl ester; hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 74 percent / Et3N, DCC, DMAP / CH2Cl2 / 24 h / 25 °C 2: 90 percent / LiOH*H2O / tetrahydrofuran; methanol; H2O / 3 h / 25 °C 3: 50 percent / DMAP, DCC / CH2Cl2 / 24 h / 0 °C 4: 3M HCl / ethyl acetate / 0.5 h / 25 °C
Multi-step reaction with 4 steps 1: 85 percent / Et3N, DMAP, DCC / CH2Cl2 / 24 h / 25 °C 2: H2 / 10percent Pd/C / methanol / 16 h / 25 °C / 760 Torr 3: 50 percent / DMAP, DCC / CH2Cl2 / 24 h / 0 °C 4: 3M HCl / ethyl acetate / 0.5 h / 25 °C
Multi-step reaction with 4 steps 1: 74 percent / DCC, Et3N, DMAP / CH2Cl2 / 24 h / 25 °C 2: 90 percent / aq. LiOH / tetrahydrofuran; methanol / 3 h / 25 °C 3: 71 percent / DCC, DMAP / CH2Cl2 / 24 h / 0 °C 4: 100 percent / 3 M HCl / ethyl acetate / 0.5 h / 25 °C
  • 18
  • [ 133498-97-2 ]
  • [ 151961-28-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 9 steps 1: 74 percent / Et3N, DCC, DMAP / CH2Cl2 / 24 h / 25 °C 2: 90 percent / LiOH*H2O / tetrahydrofuran; methanol; H2O / 3 h / 25 °C 3: 50 percent / DMAP, DCC / CH2Cl2 / 24 h / 0 °C 4: H2 / 10percent Pd/C / methanol / 12 h / 25 °C 5: 80 percent / NaHCO3, HOBt, EDCl / dimethylformamide / a) 0 deg C, 2 h, b) 25 deg C, 24 h 6: 97 percent / H2 / 10percent Pd/C / methanol / 16 h / 760 Torr 7: 100 percent / 3M HCl / ethyl acetate / 0.5 h / 25 °C 8: 89 percent / NaHCO3, diphenyl phosphorazidate / dimethylformamide / 72 h / 0 °C 9: 73 percent / Bu4NF / tetrahydrofuran / 48 h / 25 °C
Multi-step reaction with 9 steps 1: 74 percent / Et3N, DCC, DMAP / CH2Cl2 / 24 h / 25 °C 2: 90 percent / LiOH*H2O / tetrahydrofuran; methanol; H2O / 3 h / 25 °C 3: 50 percent / DMAP, DCC / CH2Cl2 / 24 h / 0 °C 4: H2 / 10percent Pd/C / methanol / 12 h / 25 °C 5: 80 percent / NaHCO3, HOBt, EDCl / dimethylformamide / a) 0 deg C, 2 h, b) 25 deg C, 24 h 6: 97 percent / H2 / 10percent Pd/C / methanol / 16 h / 760 Torr 7: 100 percent / 3M HCl / ethyl acetate / 0.5 h / 25 °C 8: 89 percent / NaHCO3, diphenyl phosphorazidate / dimethylformamide / 72 h / 0 °C 9: 27 percent / Bu4NF / tetrahydrofuran / 24 h / 25 °C
Multi-step reaction with 9 steps 1: 74 percent / Et3N, DCC, DMAP / CH2Cl2 / 24 h / 25 °C 2: 90 percent / LiOH*H2O / tetrahydrofuran; methanol; H2O / 3 h / 25 °C 3: 50 percent / DMAP, DCC / CH2Cl2 / 24 h / 0 °C 4: 3M HCl / ethyl acetate / 0.5 h / 25 °C 5: 80 percent / NaHCO3, HOBt, EDCl / dimethylformamide / a) 0 deg C, 2 h, b) 25 deg C, 24 h 6: 97 percent / H2 / 10percent Pd/C / methanol / 16 h / 760 Torr 7: 100 percent / 3M HCl / ethyl acetate / 0.5 h / 25 °C 8: 89 percent / NaHCO3, diphenyl phosphorazidate / dimethylformamide / 72 h / 0 °C 9: 73 percent / Bu4NF / tetrahydrofuran / 48 h / 25 °C
Multi-step reaction with 9 steps 1: 74 percent / Et3N, DCC, DMAP / CH2Cl2 / 24 h / 25 °C 2: 90 percent / LiOH*H2O / tetrahydrofuran; methanol; H2O / 3 h / 25 °C 3: 50 percent / DMAP, DCC / CH2Cl2 / 24 h / 0 °C 4: 3M HCl / ethyl acetate / 0.5 h / 25 °C 5: 80 percent / NaHCO3, HOBt, EDCl / dimethylformamide / a) 0 deg C, 2 h, b) 25 deg C, 24 h 6: 97 percent / H2 / 10percent Pd/C / methanol / 16 h / 760 Torr 7: 100 percent / 3M HCl / ethyl acetate / 0.5 h / 25 °C 8: 89 percent / NaHCO3, diphenyl phosphorazidate / dimethylformamide / 72 h / 0 °C 9: 27 percent / Bu4NF / tetrahydrofuran / 24 h / 25 °C
Multi-step reaction with 9 steps 1: 85 percent / Et3N, DMAP, DCC / CH2Cl2 / 24 h / 25 °C 2: H2 / 10percent Pd/C / methanol / 16 h / 25 °C / 760 Torr 3: 50 percent / DMAP, DCC / CH2Cl2 / 24 h / 0 °C 4: H2 / 10percent Pd/C / methanol / 12 h / 25 °C 5: 80 percent / NaHCO3, HOBt, EDCl / dimethylformamide / a) 0 deg C, 2 h, b) 25 deg C, 24 h 6: 97 percent / H2 / 10percent Pd/C / methanol / 16 h / 760 Torr 7: 100 percent / 3M HCl / ethyl acetate / 0.5 h / 25 °C 8: 89 percent / NaHCO3, diphenyl phosphorazidate / dimethylformamide / 72 h / 0 °C 9: 73 percent / Bu4NF / tetrahydrofuran / 48 h / 25 °C
Multi-step reaction with 9 steps 1: 85 percent / Et3N, DMAP, DCC / CH2Cl2 / 24 h / 25 °C 2: H2 / 10percent Pd/C / methanol / 16 h / 25 °C / 760 Torr 3: 50 percent / DMAP, DCC / CH2Cl2 / 24 h / 0 °C 4: H2 / 10percent Pd/C / methanol / 12 h / 25 °C 5: 80 percent / NaHCO3, HOBt, EDCl / dimethylformamide / a) 0 deg C, 2 h, b) 25 deg C, 24 h 6: 97 percent / H2 / 10percent Pd/C / methanol / 16 h / 760 Torr 7: 100 percent / 3M HCl / ethyl acetate / 0.5 h / 25 °C 8: 89 percent / NaHCO3, diphenyl phosphorazidate / dimethylformamide / 72 h / 0 °C 9: 27 percent / Bu4NF / tetrahydrofuran / 24 h / 25 °C
Multi-step reaction with 9 steps 1: 85 percent / Et3N, DMAP, DCC / CH2Cl2 / 24 h / 25 °C 2: H2 / 10percent Pd/C / methanol / 16 h / 25 °C / 760 Torr 3: 50 percent / DMAP, DCC / CH2Cl2 / 24 h / 0 °C 4: 3M HCl / ethyl acetate / 0.5 h / 25 °C 5: 80 percent / NaHCO3, HOBt, EDCl / dimethylformamide / a) 0 deg C, 2 h, b) 25 deg C, 24 h 6: 97 percent / H2 / 10percent Pd/C / methanol / 16 h / 760 Torr 7: 100 percent / 3M HCl / ethyl acetate / 0.5 h / 25 °C 8: 89 percent / NaHCO3, diphenyl phosphorazidate / dimethylformamide / 72 h / 0 °C 9: 73 percent / Bu4NF / tetrahydrofuran / 48 h / 25 °C
Multi-step reaction with 9 steps 1: 85 percent / Et3N, DMAP, DCC / CH2Cl2 / 24 h / 25 °C 2: H2 / 10percent Pd/C / methanol / 16 h / 25 °C / 760 Torr 3: 50 percent / DMAP, DCC / CH2Cl2 / 24 h / 0 °C 4: 3M HCl / ethyl acetate / 0.5 h / 25 °C 5: 80 percent / NaHCO3, HOBt, EDCl / dimethylformamide / a) 0 deg C, 2 h, b) 25 deg C, 24 h 6: 97 percent / H2 / 10percent Pd/C / methanol / 16 h / 760 Torr 7: 100 percent / 3M HCl / ethyl acetate / 0.5 h / 25 °C 8: 89 percent / NaHCO3, diphenyl phosphorazidate / dimethylformamide / 72 h / 0 °C 9: 27 percent / Bu4NF / tetrahydrofuran / 24 h / 25 °C
Multi-step reaction with 9 steps 1: 74 percent / DCC, Et3N, DMAP / CH2Cl2 / 24 h / 25 °C 2: 90 percent / aq. LiOH / tetrahydrofuran; methanol / 3 h / 25 °C 3: 71 percent / DCC, DMAP / CH2Cl2 / 24 h / 0 °C 4: 98 percent / H2 / 10percent Pd/C / methanol / 12 h / 25 °C 5: 81 percent / EDCI, HOBt, NaHCO3 / CH2Cl2 / 24 h / 25 °C 6: H2 / 10percent Pd/C / methanol / 12 h / 25 °C 7: 3 M HCl / ethyl acetate / 0.5 h / 25 °C 8: diphenyl phosphorazidate (DPPA), NaHCO3 / dimethylformamide / 48 h / 0 °C 9: 77 percent / Bu4NF / tetrahydrofuran / 48 h / 25 °C
Multi-step reaction with 9 steps 1: 74 percent / DCC, Et3N, DMAP / CH2Cl2 / 24 h / 25 °C 2: 90 percent / aq. LiOH / tetrahydrofuran; methanol / 3 h / 25 °C 3: 71 percent / DCC, DMAP / CH2Cl2 / 24 h / 0 °C 4: 100 percent / 3 M HCl / ethyl acetate / 0.5 h / 25 °C 5: 81 percent / EDCI, HOBt, NaHCO3 / CH2Cl2 / 24 h / 25 °C 6: H2 / 10percent Pd/C / methanol / 12 h / 25 °C 7: 3 M HCl / ethyl acetate / 0.5 h / 25 °C 8: diphenyl phosphorazidate (DPPA), NaHCO3 / dimethylformamide / 48 h / 0 °C 9: 77 percent / Bu4NF / tetrahydrofuran / 48 h / 25 °C

  • 19
  • [ 133498-97-2 ]
  • (3R,7S,16S,23R,27S,36S)-3,23-Diamino-7,27-diisopropyl-8,11,28,31-tetramethyl-5,25-dioxa-1,8,11,14,21,28,31,34-octaaza-tricyclo[34.4.0.016,21]tetracontane-2,6,9,12,15,22,26,29,32,35-decaone; hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 10 steps 1: 74 percent / Et3N, DCC, DMAP / CH2Cl2 / 24 h / 25 °C 2: 90 percent / LiOH*H2O / tetrahydrofuran; methanol; H2O / 3 h / 25 °C 3: 50 percent / DMAP, DCC / CH2Cl2 / 24 h / 0 °C 4: H2 / 10percent Pd/C / methanol / 12 h / 25 °C 5: 80 percent / NaHCO3, HOBt, EDCl / dimethylformamide / a) 0 deg C, 2 h, b) 25 deg C, 24 h 6: 97 percent / H2 / 10percent Pd/C / methanol / 16 h / 760 Torr 7: 100 percent / 3M HCl / ethyl acetate / 0.5 h / 25 °C 8: 89 percent / NaHCO3, diphenyl phosphorazidate / dimethylformamide / 72 h / 0 °C 9: 73 percent / Bu4NF / tetrahydrofuran / 48 h / 25 °C 10: 100 percent / 3 M HCl / ethyl acetate / 0.5 h / 25 °C
Multi-step reaction with 10 steps 1: 74 percent / Et3N, DCC, DMAP / CH2Cl2 / 24 h / 25 °C 2: 90 percent / LiOH*H2O / tetrahydrofuran; methanol; H2O / 3 h / 25 °C 3: 50 percent / DMAP, DCC / CH2Cl2 / 24 h / 0 °C 4: H2 / 10percent Pd/C / methanol / 12 h / 25 °C 5: 80 percent / NaHCO3, HOBt, EDCl / dimethylformamide / a) 0 deg C, 2 h, b) 25 deg C, 24 h 6: 97 percent / H2 / 10percent Pd/C / methanol / 16 h / 760 Torr 7: 100 percent / 3M HCl / ethyl acetate / 0.5 h / 25 °C 8: 89 percent / NaHCO3, diphenyl phosphorazidate / dimethylformamide / 72 h / 0 °C 9: 27 percent / Bu4NF / tetrahydrofuran / 24 h / 25 °C 10: 100 percent / 3 M HCl / ethyl acetate / 0.5 h / 25 °C
Multi-step reaction with 10 steps 1: 74 percent / Et3N, DCC, DMAP / CH2Cl2 / 24 h / 25 °C 2: 90 percent / LiOH*H2O / tetrahydrofuran; methanol; H2O / 3 h / 25 °C 3: 50 percent / DMAP, DCC / CH2Cl2 / 24 h / 0 °C 4: 3M HCl / ethyl acetate / 0.5 h / 25 °C 5: 80 percent / NaHCO3, HOBt, EDCl / dimethylformamide / a) 0 deg C, 2 h, b) 25 deg C, 24 h 6: 97 percent / H2 / 10percent Pd/C / methanol / 16 h / 760 Torr 7: 100 percent / 3M HCl / ethyl acetate / 0.5 h / 25 °C 8: 89 percent / NaHCO3, diphenyl phosphorazidate / dimethylformamide / 72 h / 0 °C 9: 73 percent / Bu4NF / tetrahydrofuran / 48 h / 25 °C 10: 100 percent / 3 M HCl / ethyl acetate / 0.5 h / 25 °C
Multi-step reaction with 10 steps 1: 74 percent / Et3N, DCC, DMAP / CH2Cl2 / 24 h / 25 °C 2: 90 percent / LiOH*H2O / tetrahydrofuran; methanol; H2O / 3 h / 25 °C 3: 50 percent / DMAP, DCC / CH2Cl2 / 24 h / 0 °C 4: 3M HCl / ethyl acetate / 0.5 h / 25 °C 5: 80 percent / NaHCO3, HOBt, EDCl / dimethylformamide / a) 0 deg C, 2 h, b) 25 deg C, 24 h 6: 97 percent / H2 / 10percent Pd/C / methanol / 16 h / 760 Torr 7: 100 percent / 3M HCl / ethyl acetate / 0.5 h / 25 °C 8: 89 percent / NaHCO3, diphenyl phosphorazidate / dimethylformamide / 72 h / 0 °C 9: 27 percent / Bu4NF / tetrahydrofuran / 24 h / 25 °C 10: 100 percent / 3 M HCl / ethyl acetate / 0.5 h / 25 °C
Multi-step reaction with 10 steps 1: 85 percent / Et3N, DMAP, DCC / CH2Cl2 / 24 h / 25 °C 2: H2 / 10percent Pd/C / methanol / 16 h / 25 °C / 760 Torr 3: 50 percent / DMAP, DCC / CH2Cl2 / 24 h / 0 °C 4: H2 / 10percent Pd/C / methanol / 12 h / 25 °C 5: 80 percent / NaHCO3, HOBt, EDCl / dimethylformamide / a) 0 deg C, 2 h, b) 25 deg C, 24 h 6: 97 percent / H2 / 10percent Pd/C / methanol / 16 h / 760 Torr 7: 100 percent / 3M HCl / ethyl acetate / 0.5 h / 25 °C 8: 89 percent / NaHCO3, diphenyl phosphorazidate / dimethylformamide / 72 h / 0 °C 9: 73 percent / Bu4NF / tetrahydrofuran / 48 h / 25 °C 10: 100 percent / 3 M HCl / ethyl acetate / 0.5 h / 25 °C
Multi-step reaction with 10 steps 1: 85 percent / Et3N, DMAP, DCC / CH2Cl2 / 24 h / 25 °C 2: H2 / 10percent Pd/C / methanol / 16 h / 25 °C / 760 Torr 3: 50 percent / DMAP, DCC / CH2Cl2 / 24 h / 0 °C 4: H2 / 10percent Pd/C / methanol / 12 h / 25 °C 5: 80 percent / NaHCO3, HOBt, EDCl / dimethylformamide / a) 0 deg C, 2 h, b) 25 deg C, 24 h 6: 97 percent / H2 / 10percent Pd/C / methanol / 16 h / 760 Torr 7: 100 percent / 3M HCl / ethyl acetate / 0.5 h / 25 °C 8: 89 percent / NaHCO3, diphenyl phosphorazidate / dimethylformamide / 72 h / 0 °C 9: 27 percent / Bu4NF / tetrahydrofuran / 24 h / 25 °C 10: 100 percent / 3 M HCl / ethyl acetate / 0.5 h / 25 °C
Multi-step reaction with 10 steps 1: 85 percent / Et3N, DMAP, DCC / CH2Cl2 / 24 h / 25 °C 2: H2 / 10percent Pd/C / methanol / 16 h / 25 °C / 760 Torr 3: 50 percent / DMAP, DCC / CH2Cl2 / 24 h / 0 °C 4: 3M HCl / ethyl acetate / 0.5 h / 25 °C 5: 80 percent / NaHCO3, HOBt, EDCl / dimethylformamide / a) 0 deg C, 2 h, b) 25 deg C, 24 h 6: 97 percent / H2 / 10percent Pd/C / methanol / 16 h / 760 Torr 7: 100 percent / 3M HCl / ethyl acetate / 0.5 h / 25 °C 8: 89 percent / NaHCO3, diphenyl phosphorazidate / dimethylformamide / 72 h / 0 °C 9: 73 percent / Bu4NF / tetrahydrofuran / 48 h / 25 °C 10: 100 percent / 3 M HCl / ethyl acetate / 0.5 h / 25 °C
Multi-step reaction with 10 steps 1: 85 percent / Et3N, DMAP, DCC / CH2Cl2 / 24 h / 25 °C 2: H2 / 10percent Pd/C / methanol / 16 h / 25 °C / 760 Torr 3: 50 percent / DMAP, DCC / CH2Cl2 / 24 h / 0 °C 4: 3M HCl / ethyl acetate / 0.5 h / 25 °C 5: 80 percent / NaHCO3, HOBt, EDCl / dimethylformamide / a) 0 deg C, 2 h, b) 25 deg C, 24 h 6: 97 percent / H2 / 10percent Pd/C / methanol / 16 h / 760 Torr 7: 100 percent / 3M HCl / ethyl acetate / 0.5 h / 25 °C 8: 89 percent / NaHCO3, diphenyl phosphorazidate / dimethylformamide / 72 h / 0 °C 9: 27 percent / Bu4NF / tetrahydrofuran / 24 h / 25 °C 10: 100 percent / 3 M HCl / ethyl acetate / 0.5 h / 25 °C
Multi-step reaction with 10 steps 1: 74 percent / DCC, Et3N, DMAP / CH2Cl2 / 24 h / 25 °C 2: 90 percent / aq. LiOH / tetrahydrofuran; methanol / 3 h / 25 °C 3: 71 percent / DCC, DMAP / CH2Cl2 / 24 h / 0 °C 4: 98 percent / H2 / 10percent Pd/C / methanol / 12 h / 25 °C 5: 81 percent / EDCI, HOBt, NaHCO3 / CH2Cl2 / 24 h / 25 °C 6: H2 / 10percent Pd/C / methanol / 12 h / 25 °C 7: 3 M HCl / ethyl acetate / 0.5 h / 25 °C 8: diphenyl phosphorazidate (DPPA), NaHCO3 / dimethylformamide / 48 h / 0 °C 9: 77 percent / Bu4NF / tetrahydrofuran / 48 h / 25 °C 10: 3 M HCl / ethyl acetate / 0.5 h / 25 °C
Multi-step reaction with 10 steps 1: 74 percent / DCC, Et3N, DMAP / CH2Cl2 / 24 h / 25 °C 2: 90 percent / aq. LiOH / tetrahydrofuran; methanol / 3 h / 25 °C 3: 71 percent / DCC, DMAP / CH2Cl2 / 24 h / 0 °C 4: 100 percent / 3 M HCl / ethyl acetate / 0.5 h / 25 °C 5: 81 percent / EDCI, HOBt, NaHCO3 / CH2Cl2 / 24 h / 25 °C 6: H2 / 10percent Pd/C / methanol / 12 h / 25 °C 7: 3 M HCl / ethyl acetate / 0.5 h / 25 °C 8: diphenyl phosphorazidate (DPPA), NaHCO3 / dimethylformamide / 48 h / 0 °C 9: 77 percent / Bu4NF / tetrahydrofuran / 48 h / 25 °C 10: 3 M HCl / ethyl acetate / 0.5 h / 25 °C

  • 20
  • [ 133498-97-2 ]
  • [ 151961-27-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1: 74 percent / Et3N, DCC, DMAP / CH2Cl2 / 24 h / 25 °C 2: 90 percent / LiOH*H2O / tetrahydrofuran; methanol; H2O / 3 h / 25 °C 3: 50 percent / DMAP, DCC / CH2Cl2 / 24 h / 0 °C 4: H2 / 10percent Pd/C / methanol / 12 h / 25 °C 5: 80 percent / NaHCO3, HOBt, EDCl / dimethylformamide / a) 0 deg C, 2 h, b) 25 deg C, 24 h 6: 97 percent / H2 / 10percent Pd/C / methanol / 16 h / 760 Torr 7: 100 percent / 3M HCl / ethyl acetate / 0.5 h / 25 °C 8: 89 percent / NaHCO3, diphenyl phosphorazidate / dimethylformamide / 72 h / 0 °C
Multi-step reaction with 8 steps 1: 74 percent / Et3N, DCC, DMAP / CH2Cl2 / 24 h / 25 °C 2: 90 percent / LiOH*H2O / tetrahydrofuran; methanol; H2O / 3 h / 25 °C 3: 50 percent / DMAP, DCC / CH2Cl2 / 24 h / 0 °C 4: 3M HCl / ethyl acetate / 0.5 h / 25 °C 5: 80 percent / NaHCO3, HOBt, EDCl / dimethylformamide / a) 0 deg C, 2 h, b) 25 deg C, 24 h 6: 97 percent / H2 / 10percent Pd/C / methanol / 16 h / 760 Torr 7: 100 percent / 3M HCl / ethyl acetate / 0.5 h / 25 °C 8: 89 percent / NaHCO3, diphenyl phosphorazidate / dimethylformamide / 72 h / 0 °C
Multi-step reaction with 8 steps 1: 85 percent / Et3N, DMAP, DCC / CH2Cl2 / 24 h / 25 °C 2: H2 / 10percent Pd/C / methanol / 16 h / 25 °C / 760 Torr 3: 50 percent / DMAP, DCC / CH2Cl2 / 24 h / 0 °C 4: H2 / 10percent Pd/C / methanol / 12 h / 25 °C 5: 80 percent / NaHCO3, HOBt, EDCl / dimethylformamide / a) 0 deg C, 2 h, b) 25 deg C, 24 h 6: 97 percent / H2 / 10percent Pd/C / methanol / 16 h / 760 Torr 7: 100 percent / 3M HCl / ethyl acetate / 0.5 h / 25 °C 8: 89 percent / NaHCO3, diphenyl phosphorazidate / dimethylformamide / 72 h / 0 °C
Multi-step reaction with 8 steps 1: 85 percent / Et3N, DMAP, DCC / CH2Cl2 / 24 h / 25 °C 2: H2 / 10percent Pd/C / methanol / 16 h / 25 °C / 760 Torr 3: 50 percent / DMAP, DCC / CH2Cl2 / 24 h / 0 °C 4: 3M HCl / ethyl acetate / 0.5 h / 25 °C 5: 80 percent / NaHCO3, HOBt, EDCl / dimethylformamide / a) 0 deg C, 2 h, b) 25 deg C, 24 h 6: 97 percent / H2 / 10percent Pd/C / methanol / 16 h / 760 Torr 7: 100 percent / 3M HCl / ethyl acetate / 0.5 h / 25 °C 8: 89 percent / NaHCO3, diphenyl phosphorazidate / dimethylformamide / 72 h / 0 °C
Multi-step reaction with 8 steps 1: 74 percent / DCC, Et3N, DMAP / CH2Cl2 / 24 h / 25 °C 2: 90 percent / aq. LiOH / tetrahydrofuran; methanol / 3 h / 25 °C 3: 71 percent / DCC, DMAP / CH2Cl2 / 24 h / 0 °C 4: 98 percent / H2 / 10percent Pd/C / methanol / 12 h / 25 °C 5: 81 percent / EDCI, HOBt, NaHCO3 / CH2Cl2 / 24 h / 25 °C 6: H2 / 10percent Pd/C / methanol / 12 h / 25 °C 7: 3 M HCl / ethyl acetate / 0.5 h / 25 °C 8: diphenyl phosphorazidate (DPPA), NaHCO3 / dimethylformamide / 48 h / 0 °C
Multi-step reaction with 8 steps 1: 74 percent / DCC, Et3N, DMAP / CH2Cl2 / 24 h / 25 °C 2: 90 percent / aq. LiOH / tetrahydrofuran; methanol / 3 h / 25 °C 3: 71 percent / DCC, DMAP / CH2Cl2 / 24 h / 0 °C 4: 100 percent / 3 M HCl / ethyl acetate / 0.5 h / 25 °C 5: 81 percent / EDCI, HOBt, NaHCO3 / CH2Cl2 / 24 h / 25 °C 6: H2 / 10percent Pd/C / methanol / 12 h / 25 °C 7: 3 M HCl / ethyl acetate / 0.5 h / 25 °C 8: diphenyl phosphorazidate (DPPA), NaHCO3 / dimethylformamide / 48 h / 0 °C

  • 21
  • [ 133498-97-2 ]
  • N1-SES-N6-<(3-hydroxylquinolyl)-2-carbonyl>-(D-Ser-Pip-Gly-Sar-NMe-Val)2(serine hydroxyl) dilactone [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 12 steps 1: 74 percent / Et3N, DCC, DMAP / CH2Cl2 / 24 h / 25 °C 2: 90 percent / LiOH*H2O / tetrahydrofuran; methanol; H2O / 3 h / 25 °C 3: 50 percent / DMAP, DCC / CH2Cl2 / 24 h / 0 °C 4: H2 / 10percent Pd/C / methanol / 12 h / 25 °C 5: 80 percent / NaHCO3, HOBt, EDCl / dimethylformamide / a) 0 deg C, 2 h, b) 25 deg C, 24 h 6: 97 percent / H2 / 10percent Pd/C / methanol / 16 h / 760 Torr 7: 100 percent / 3M HCl / ethyl acetate / 0.5 h / 25 °C 8: 89 percent / NaHCO3, diphenyl phosphorazidate / dimethylformamide / 72 h / 0 °C 9: 33 percent / Bu4NF / tetrahydrofuran / 24 h / 25 °C 10: 100 percent / 3 M HCl / ethyl acetate / 0.5 h / 25 °C 11: 63 percent / NaHCO3, HOBt, EDCl / dimethylformamide / 48 h / 25 °C 12: 86 percent / H2 / 10percent Pd/C / ethyl acetate / 14 h / 25 °C / 760 Torr
Multi-step reaction with 12 steps 1: 74 percent / Et3N, DCC, DMAP / CH2Cl2 / 24 h / 25 °C 2: 90 percent / LiOH*H2O / tetrahydrofuran; methanol; H2O / 3 h / 25 °C 3: 50 percent / DMAP, DCC / CH2Cl2 / 24 h / 0 °C 4: 3M HCl / ethyl acetate / 0.5 h / 25 °C 5: 80 percent / NaHCO3, HOBt, EDCl / dimethylformamide / a) 0 deg C, 2 h, b) 25 deg C, 24 h 6: 97 percent / H2 / 10percent Pd/C / methanol / 16 h / 760 Torr 7: 100 percent / 3M HCl / ethyl acetate / 0.5 h / 25 °C 8: 89 percent / NaHCO3, diphenyl phosphorazidate / dimethylformamide / 72 h / 0 °C 9: 33 percent / Bu4NF / tetrahydrofuran / 24 h / 25 °C 10: 100 percent / 3 M HCl / ethyl acetate / 0.5 h / 25 °C 11: 63 percent / NaHCO3, HOBt, EDCl / dimethylformamide / 48 h / 25 °C 12: 86 percent / H2 / 10percent Pd/C / ethyl acetate / 14 h / 25 °C / 760 Torr
Multi-step reaction with 12 steps 1: 85 percent / Et3N, DMAP, DCC / CH2Cl2 / 24 h / 25 °C 2: H2 / 10percent Pd/C / methanol / 16 h / 25 °C / 760 Torr 3: 50 percent / DMAP, DCC / CH2Cl2 / 24 h / 0 °C 4: H2 / 10percent Pd/C / methanol / 12 h / 25 °C 5: 80 percent / NaHCO3, HOBt, EDCl / dimethylformamide / a) 0 deg C, 2 h, b) 25 deg C, 24 h 6: 97 percent / H2 / 10percent Pd/C / methanol / 16 h / 760 Torr 7: 100 percent / 3M HCl / ethyl acetate / 0.5 h / 25 °C 8: 89 percent / NaHCO3, diphenyl phosphorazidate / dimethylformamide / 72 h / 0 °C 9: 33 percent / Bu4NF / tetrahydrofuran / 24 h / 25 °C 10: 100 percent / 3 M HCl / ethyl acetate / 0.5 h / 25 °C 11: 63 percent / NaHCO3, HOBt, EDCl / dimethylformamide / 48 h / 25 °C 12: 86 percent / H2 / 10percent Pd/C / ethyl acetate / 14 h / 25 °C / 760 Torr
Multi-step reaction with 12 steps 1: 85 percent / Et3N, DMAP, DCC / CH2Cl2 / 24 h / 25 °C 2: H2 / 10percent Pd/C / methanol / 16 h / 25 °C / 760 Torr 3: 50 percent / DMAP, DCC / CH2Cl2 / 24 h / 0 °C 4: 3M HCl / ethyl acetate / 0.5 h / 25 °C 5: 80 percent / NaHCO3, HOBt, EDCl / dimethylformamide / a) 0 deg C, 2 h, b) 25 deg C, 24 h 6: 97 percent / H2 / 10percent Pd/C / methanol / 16 h / 760 Torr 7: 100 percent / 3M HCl / ethyl acetate / 0.5 h / 25 °C 8: 89 percent / NaHCO3, diphenyl phosphorazidate / dimethylformamide / 72 h / 0 °C 9: 33 percent / Bu4NF / tetrahydrofuran / 24 h / 25 °C 10: 100 percent / 3 M HCl / ethyl acetate / 0.5 h / 25 °C 11: 63 percent / NaHCO3, HOBt, EDCl / dimethylformamide / 48 h / 25 °C 12: 86 percent / H2 / 10percent Pd/C / ethyl acetate / 14 h / 25 °C / 760 Torr

  • 22
  • [ 133498-97-2 ]
  • 2-Trimethylsilanyl-ethanesulfonic acid ((3R,7S,16S,23R,27S,36S)-23-amino-7,27-diisopropyl-8,11,28,31-tetramethyl-2,6,9,12,15,22,26,29,32,35-decaoxo-5,25-dioxa-1,8,11,14,21,28,31,34-octaaza-tricyclo[34.4.0.016,21]tetracont-3-yl)-amide; hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 10 steps 1: 74 percent / Et3N, DCC, DMAP / CH2Cl2 / 24 h / 25 °C 2: 90 percent / LiOH*H2O / tetrahydrofuran; methanol; H2O / 3 h / 25 °C 3: 50 percent / DMAP, DCC / CH2Cl2 / 24 h / 0 °C 4: H2 / 10percent Pd/C / methanol / 12 h / 25 °C 5: 80 percent / NaHCO3, HOBt, EDCl / dimethylformamide / a) 0 deg C, 2 h, b) 25 deg C, 24 h 6: 97 percent / H2 / 10percent Pd/C / methanol / 16 h / 760 Torr 7: 100 percent / 3M HCl / ethyl acetate / 0.5 h / 25 °C 8: 89 percent / NaHCO3, diphenyl phosphorazidate / dimethylformamide / 72 h / 0 °C 9: 33 percent / Bu4NF / tetrahydrofuran / 24 h / 25 °C 10: 100 percent / 3 M HCl / ethyl acetate / 0.5 h / 25 °C
Multi-step reaction with 10 steps 1: 74 percent / Et3N, DCC, DMAP / CH2Cl2 / 24 h / 25 °C 2: 90 percent / LiOH*H2O / tetrahydrofuran; methanol; H2O / 3 h / 25 °C 3: 50 percent / DMAP, DCC / CH2Cl2 / 24 h / 0 °C 4: 3M HCl / ethyl acetate / 0.5 h / 25 °C 5: 80 percent / NaHCO3, HOBt, EDCl / dimethylformamide / a) 0 deg C, 2 h, b) 25 deg C, 24 h 6: 97 percent / H2 / 10percent Pd/C / methanol / 16 h / 760 Torr 7: 100 percent / 3M HCl / ethyl acetate / 0.5 h / 25 °C 8: 89 percent / NaHCO3, diphenyl phosphorazidate / dimethylformamide / 72 h / 0 °C 9: 33 percent / Bu4NF / tetrahydrofuran / 24 h / 25 °C 10: 100 percent / 3 M HCl / ethyl acetate / 0.5 h / 25 °C
Multi-step reaction with 10 steps 1: 85 percent / Et3N, DMAP, DCC / CH2Cl2 / 24 h / 25 °C 2: H2 / 10percent Pd/C / methanol / 16 h / 25 °C / 760 Torr 3: 50 percent / DMAP, DCC / CH2Cl2 / 24 h / 0 °C 4: H2 / 10percent Pd/C / methanol / 12 h / 25 °C 5: 80 percent / NaHCO3, HOBt, EDCl / dimethylformamide / a) 0 deg C, 2 h, b) 25 deg C, 24 h 6: 97 percent / H2 / 10percent Pd/C / methanol / 16 h / 760 Torr 7: 100 percent / 3M HCl / ethyl acetate / 0.5 h / 25 °C 8: 89 percent / NaHCO3, diphenyl phosphorazidate / dimethylformamide / 72 h / 0 °C 9: 33 percent / Bu4NF / tetrahydrofuran / 24 h / 25 °C 10: 100 percent / 3 M HCl / ethyl acetate / 0.5 h / 25 °C
Multi-step reaction with 10 steps 1: 85 percent / Et3N, DMAP, DCC / CH2Cl2 / 24 h / 25 °C 2: H2 / 10percent Pd/C / methanol / 16 h / 25 °C / 760 Torr 3: 50 percent / DMAP, DCC / CH2Cl2 / 24 h / 0 °C 4: 3M HCl / ethyl acetate / 0.5 h / 25 °C 5: 80 percent / NaHCO3, HOBt, EDCl / dimethylformamide / a) 0 deg C, 2 h, b) 25 deg C, 24 h 6: 97 percent / H2 / 10percent Pd/C / methanol / 16 h / 760 Torr 7: 100 percent / 3M HCl / ethyl acetate / 0.5 h / 25 °C 8: 89 percent / NaHCO3, diphenyl phosphorazidate / dimethylformamide / 72 h / 0 °C 9: 33 percent / Bu4NF / tetrahydrofuran / 24 h / 25 °C 10: 100 percent / 3 M HCl / ethyl acetate / 0.5 h / 25 °C

  • 23
  • [ 133498-97-2 ]
  • [ 174311-16-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 11 steps 1: 74 percent / Et3N, DCC, DMAP / CH2Cl2 / 24 h / 25 °C 2: 90 percent / LiOH*H2O / tetrahydrofuran; methanol; H2O / 3 h / 25 °C 3: 50 percent / DMAP, DCC / CH2Cl2 / 24 h / 0 °C 4: H2 / 10percent Pd/C / methanol / 12 h / 25 °C 5: 80 percent / NaHCO3, HOBt, EDCl / dimethylformamide / a) 0 deg C, 2 h, b) 25 deg C, 24 h 6: 97 percent / H2 / 10percent Pd/C / methanol / 16 h / 760 Torr 7: 100 percent / 3M HCl / ethyl acetate / 0.5 h / 25 °C 8: 89 percent / NaHCO3, diphenyl phosphorazidate / dimethylformamide / 72 h / 0 °C 9: 33 percent / Bu4NF / tetrahydrofuran / 24 h / 25 °C 10: 100 percent / 3 M HCl / ethyl acetate / 0.5 h / 25 °C 11: 63 percent / NaHCO3, HOBt, EDCl / dimethylformamide / 48 h / 25 °C
Multi-step reaction with 11 steps 1: 74 percent / Et3N, DCC, DMAP / CH2Cl2 / 24 h / 25 °C 2: 90 percent / LiOH*H2O / tetrahydrofuran; methanol; H2O / 3 h / 25 °C 3: 50 percent / DMAP, DCC / CH2Cl2 / 24 h / 0 °C 4: 3M HCl / ethyl acetate / 0.5 h / 25 °C 5: 80 percent / NaHCO3, HOBt, EDCl / dimethylformamide / a) 0 deg C, 2 h, b) 25 deg C, 24 h 6: 97 percent / H2 / 10percent Pd/C / methanol / 16 h / 760 Torr 7: 100 percent / 3M HCl / ethyl acetate / 0.5 h / 25 °C 8: 89 percent / NaHCO3, diphenyl phosphorazidate / dimethylformamide / 72 h / 0 °C 9: 33 percent / Bu4NF / tetrahydrofuran / 24 h / 25 °C 10: 100 percent / 3 M HCl / ethyl acetate / 0.5 h / 25 °C 11: 63 percent / NaHCO3, HOBt, EDCl / dimethylformamide / 48 h / 25 °C
Multi-step reaction with 11 steps 1: 85 percent / Et3N, DMAP, DCC / CH2Cl2 / 24 h / 25 °C 2: H2 / 10percent Pd/C / methanol / 16 h / 25 °C / 760 Torr 3: 50 percent / DMAP, DCC / CH2Cl2 / 24 h / 0 °C 4: H2 / 10percent Pd/C / methanol / 12 h / 25 °C 5: 80 percent / NaHCO3, HOBt, EDCl / dimethylformamide / a) 0 deg C, 2 h, b) 25 deg C, 24 h 6: 97 percent / H2 / 10percent Pd/C / methanol / 16 h / 760 Torr 7: 100 percent / 3M HCl / ethyl acetate / 0.5 h / 25 °C 8: 89 percent / NaHCO3, diphenyl phosphorazidate / dimethylformamide / 72 h / 0 °C 9: 33 percent / Bu4NF / tetrahydrofuran / 24 h / 25 °C 10: 100 percent / 3 M HCl / ethyl acetate / 0.5 h / 25 °C 11: 63 percent / NaHCO3, HOBt, EDCl / dimethylformamide / 48 h / 25 °C
Multi-step reaction with 11 steps 1: 85 percent / Et3N, DMAP, DCC / CH2Cl2 / 24 h / 25 °C 2: H2 / 10percent Pd/C / methanol / 16 h / 25 °C / 760 Torr 3: 50 percent / DMAP, DCC / CH2Cl2 / 24 h / 0 °C 4: 3M HCl / ethyl acetate / 0.5 h / 25 °C 5: 80 percent / NaHCO3, HOBt, EDCl / dimethylformamide / a) 0 deg C, 2 h, b) 25 deg C, 24 h 6: 97 percent / H2 / 10percent Pd/C / methanol / 16 h / 760 Torr 7: 100 percent / 3M HCl / ethyl acetate / 0.5 h / 25 °C 8: 89 percent / NaHCO3, diphenyl phosphorazidate / dimethylformamide / 72 h / 0 °C 9: 33 percent / Bu4NF / tetrahydrofuran / 24 h / 25 °C 10: 100 percent / 3 M HCl / ethyl acetate / 0.5 h / 25 °C 11: 63 percent / NaHCO3, HOBt, EDCl / dimethylformamide / 48 h / 25 °C

  • 24
  • [ 133498-97-2 ]
  • [ 174311-14-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 9 steps 1: 74 percent / Et3N, DCC, DMAP / CH2Cl2 / 24 h / 25 °C 2: 90 percent / LiOH*H2O / tetrahydrofuran; methanol; H2O / 3 h / 25 °C 3: 50 percent / DMAP, DCC / CH2Cl2 / 24 h / 0 °C 4: H2 / 10percent Pd/C / methanol / 12 h / 25 °C 5: 80 percent / NaHCO3, HOBt, EDCl / dimethylformamide / a) 0 deg C, 2 h, b) 25 deg C, 24 h 6: 97 percent / H2 / 10percent Pd/C / methanol / 16 h / 760 Torr 7: 100 percent / 3M HCl / ethyl acetate / 0.5 h / 25 °C 8: 89 percent / NaHCO3, diphenyl phosphorazidate / dimethylformamide / 72 h / 0 °C 9: 33 percent / Bu4NF / tetrahydrofuran / 24 h / 25 °C
Multi-step reaction with 9 steps 1: 74 percent / Et3N, DCC, DMAP / CH2Cl2 / 24 h / 25 °C 2: 90 percent / LiOH*H2O / tetrahydrofuran; methanol; H2O / 3 h / 25 °C 3: 50 percent / DMAP, DCC / CH2Cl2 / 24 h / 0 °C 4: 3M HCl / ethyl acetate / 0.5 h / 25 °C 5: 80 percent / NaHCO3, HOBt, EDCl / dimethylformamide / a) 0 deg C, 2 h, b) 25 deg C, 24 h 6: 97 percent / H2 / 10percent Pd/C / methanol / 16 h / 760 Torr 7: 100 percent / 3M HCl / ethyl acetate / 0.5 h / 25 °C 8: 89 percent / NaHCO3, diphenyl phosphorazidate / dimethylformamide / 72 h / 0 °C 9: 33 percent / Bu4NF / tetrahydrofuran / 24 h / 25 °C
Multi-step reaction with 9 steps 1: 85 percent / Et3N, DMAP, DCC / CH2Cl2 / 24 h / 25 °C 2: H2 / 10percent Pd/C / methanol / 16 h / 25 °C / 760 Torr 3: 50 percent / DMAP, DCC / CH2Cl2 / 24 h / 0 °C 4: H2 / 10percent Pd/C / methanol / 12 h / 25 °C 5: 80 percent / NaHCO3, HOBt, EDCl / dimethylformamide / a) 0 deg C, 2 h, b) 25 deg C, 24 h 6: 97 percent / H2 / 10percent Pd/C / methanol / 16 h / 760 Torr 7: 100 percent / 3M HCl / ethyl acetate / 0.5 h / 25 °C 8: 89 percent / NaHCO3, diphenyl phosphorazidate / dimethylformamide / 72 h / 0 °C 9: 33 percent / Bu4NF / tetrahydrofuran / 24 h / 25 °C
Multi-step reaction with 9 steps 1: 85 percent / Et3N, DMAP, DCC / CH2Cl2 / 24 h / 25 °C 2: H2 / 10percent Pd/C / methanol / 16 h / 25 °C / 760 Torr 3: 50 percent / DMAP, DCC / CH2Cl2 / 24 h / 0 °C 4: 3M HCl / ethyl acetate / 0.5 h / 25 °C 5: 80 percent / NaHCO3, HOBt, EDCl / dimethylformamide / a) 0 deg C, 2 h, b) 25 deg C, 24 h 6: 97 percent / H2 / 10percent Pd/C / methanol / 16 h / 760 Torr 7: 100 percent / 3M HCl / ethyl acetate / 0.5 h / 25 °C 8: 89 percent / NaHCO3, diphenyl phosphorazidate / dimethylformamide / 72 h / 0 °C 9: 33 percent / Bu4NF / tetrahydrofuran / 24 h / 25 °C

  • 25
  • [ 133498-97-2 ]
  • (S)-1-[(R)-3-[(R)-2-({2-[(2-tert-Butoxycarbonylamino-acetyl)-methyl-amino]-acetyl}-methyl-amino)-3-methyl-butyryloxy]-2-(2-trimethylsilanyl-ethanesulfonylamino)-propionyl]-piperidine-2-carboxylic acid benzyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 74 percent / Et3N, DCC, DMAP / CH2Cl2 / 24 h / 25 °C 2: 90 percent / LiOH*H2O / tetrahydrofuran; methanol; H2O / 3 h / 25 °C 3: 32 percent / DMAP, DCC / CH2Cl2 / 24 h / 0 °C
Multi-step reaction with 3 steps 1: 85 percent / Et3N, DMAP, DCC / CH2Cl2 / 24 h / 25 °C 2: H2 / 10percent Pd/C / methanol / 16 h / 25 °C / 760 Torr 3: 32 percent / DMAP, DCC / CH2Cl2 / 24 h / 0 °C
  • 26
  • [ 133498-97-2 ]
  • [ 91307-67-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: dicyclohexylcarbodiimide, 1-hydroxybenzotriazole 2: H2 / 10percent Pd/charcoal 3: HCl / dioxane
  • 27
  • [ 133498-97-2 ]
  • t-BuOCO-Gly-Sar-Gly-Gly-OH [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: dicyclohexylcarbodiimide, 1-hydroxybenzotriazole 2: H2 / 10percent Pd/charcoal
  • 28
  • [ 133498-97-2 ]
  • [ 7689-03-4 ]
  • (tert-butoxycarbonylaminoacetyl-methyl-amino)-acetic acid (S)-4-ethyl-3,13-dioxo-3,4,12,13-tetrahydro-1H-2-oxa-6,12a-diaza-dibenzo[b,h]fluoren-4-yl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
99% With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20 - 25℃; for 15h; 5.5-A [Example 5]; (Aminoacetyl-methyl-amino-acetic acid (S)-4-ethyl-3,13-dioxo-3,4,12,13-tetrahydro-1H-2-oxa-6,12a-diaza-dibenzo[b,h]fluoren-4-yl ester hydrochloride (compound 5A); [Show Image] Process 5-A; (tert-Butoxycarbonylaminoacetyl-methyl-amino)-acetic acid (S)-4-ethyl-3,13-dioxo-3,4,12,13-tetrahydro-1H-2-oxa-6,12a-diaza-dibenzo[b,h]fluoren-4-yl ester; [Show Image] 441 mg (1.93 mmol) of N-(tert-butoxycarbonyl)-glycyl]-sarcosine, 250 mg (0.77 mmol) of camptothecin, 343 mg (1.93 mmol) of 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride, and 87 mg (0.77 mmol) of 4-dimethylaminopyridine were dissolved in methylene chloride (130 mL), and then stirred at room temperature for 15 hours. The reaction solution was washed with 0.3 N aqueous hydrochloric acid and sodium hydrogen carbonate, and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. By purifying the obtained residue by silica gel column chromatography (methylene chloride:methanol = 30:1), 410 mg (99%) of (tert-butoxycarbonylaminoacetyl-methyl-amino)-acetic acid (S)-4-ethyl-3,13-dioxo-3,4,12,13-tetrahydro-1H-2-oxa-6,12a-diaza-dibenzo[b,h]fluoren-4-yl ester was obtained as a yellow solid. 1H-NMR (270MHz, CDCl3) δ(ppm): 1.00 (3H, t, J = 7.6Hz), 1.35(9H, s), 2.08-2.34 (2H, m), 3.05 (3H, s), 3.90-4.24 (3H, m), 4.61 (1H, m), 5.28 (2H, br.s), 5.40 (1H, d, J = 17.2 Hz), 5.47 (1H, br.s), 5.69 (1H, d, J = 17.2 Hz), 7.30 (1H, s), 7.68 (1H, br.t), 7.84 (1H, br.t), 7.93 (1H, br.d), 8.29 (1H, br.d), 8.40 (1H, s) FAB-MS (positive mode) m/z 577 (M+H).
99% With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 15h; 5.A Process 5-A (tert-Butoxycarbonylaminoacetyl-methyl-amino)-acetic acid (S)-4-ethyl-3,13-dioxo-3,4,12,13-tetrahydro-1H-2-oxa-6,12a-diaza-dibenzo[b,h]fluoren-4-yl ester; [Show Image] 441 mg (1.93 mmol) of N-(tert-butoxycarbonyl)-glycyl]-sarcosine, 250 mg (0.77 mmol) of camptothecin, 343 mg (1.93 mmol) of 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride, and 87 mg (0.77 mmol) of 4-dimethylaminopyridine were dissolved in methylene chloride (130 mL), and then stirred at room temperature for 15 hours. The reaction solution was washed with 0.3 N aqueous hydrochloric acid and sodium hydrogen carbonate, and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. By purifying the obtained residue by silica gel column chromatography (methylene chloride:methanol = 30:1), 410 mg (99%) of (tert-butoxycarbonylaminoacetyl-methyl-amino)-acetic acid (S)-4-ethyl-3,13-dioxo-3,4,12,13-tetrahydro-1H-2-oxa-6,12a-diaza-dibenzo[b,h]fluoren-4-yl ester was obtained as a yellow solid. 1H-NMR (270MHz, CDCl3) δ(ppm): 1.00 (3H, t, J = 7.6Hz), 1.35(9H, s), 2.08-2.34 (2H, m), 3.05 (3H, s), 3.90-4.24 (3H, m), 4.61 (1H, m), 5.28 (2H, br.s), 5.40 (1H, d, J = 17.2 Hz), 5.47 (1H, br.s), 5.69 (1H, d, J = 17.2 Hz), 7.30 (1H, s), 7.68 (1H, br.t), 7.84 (1H, br.t), 7.93 (1H, br.d), 8.29 (1H, br.d), 8.40 (1H, s) FAB-MS (positive mode) m/z 577 (M+H).
  • 29
  • [ 534605-78-2 ]
  • [ 133498-97-2 ]
  • (9S)-9-[N-(tert-butoxycarbonyl)-glycyl]-sarcosyloxy}-9-ethyl-1-pentyl-1H,12H-pyrano[3",4": 6',7']indolizino[1',2':6,5]pyrido[4,3,2-de]quinazoline-10,13(9H,15H)-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
69% With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20 - 25℃; for 1.5h; 2.2-A 1.4 g (5.67 mmol) of [N-(tert-butoxycarbonyl)-glycyl]-sarcosine, which is a known substance (), 1.3 g (2.84 mmol) of (9S)-9-ethyl-9-hydroxy-1-pentyl-1H,12H-pyrano[3',4':6',7']indolizino[1',2':6,5]pyrido[4,3,2-d e]quinazoline-10,13(9H,15H)-dione, 2.2 g (11.34 mmol) of 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride, and 1.4 g (11.34 mmol) of 4-dimethylaminopyridine were dissolved in methylene chloride (50 mL), and then stirred at room temperature for 1.5 hours. The reaction solution was washed with 0.2 N aqueous hydrochloric acid and saturated aqueous sodium hydrogen carbonate solution, then dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. Purification of the resulting residue was performed using silica gel column chromatography (methylene chloride:methanol = 100:1 to 30:1), and as a result, 1.34 g (69%) of (9S)-9-[N-(tert-butoxycarbonyl)-glycyl]-sarcosyloxy)-9-ethyl-1-pentyl-1H,12H-pyrano[3',4':6 ',7']indolizino[1',2':6,5]pyrido[4,3,2-de]quinazoline-10,13(9H,15H)-dione was obtained as a yellowish red amorphous substance. 1H-NMR (270MHz, CDCl3) δ(ppm): Rotamer A* 0.86-1.04 (6H, m), 1.24-1.53 (4H, m), 1.38 (9H, s), 1.70-1.90 (2H, m), 2.03-2.36 (2H, m), 3.04 (3H, s), 3.83 (2H, t, J = 7.1 Hz), 3.96-4.05 (2H, m), 4.12 (1H, d, J = 17.7 Hz), 4.57 (1H, d, J = 17.7 Hz), 5.21 (2H, s), 5.38 (1H, d, J = 17.3 Hz), 5.46-5.56 (1H, m), 5.66 (1H, d, J = 17.3 Hz), 7.10-7.21 (2H, m), 7.40 (1H, s), 7.60-7.75 (2H, m); Rotamer B* 0.86-1.04 (6H, m), 1.24-1.53 (4H, m), 1.38 (9H, s), 1.70-1.90 (2H, m), 2.03-2.36 (2H, m), 3.02 (3H, s), 3.83 (2H, t, J = 7.1 Hz), 3.90-3.96 (2H, m), 4.12 (1H, d, J = 17.7 Hz), 4.57 (1H, d, J = 17.7 Hz), 5.24 (2H, s), 5.38 (1H, d, J = 17.3 Hz), 5.46-5.56 (1H, m), 5.68 (1H, d, J = 17.3 Hz), 7.10-7.21 (2H, m), 7.40 (1H, s), 7.60-7.75 (2H, m). *The ratio of the two rotamers, A and B, was approximately 5:1. ESI (LC-MS positive mode) m/z 687 (M+H).
69% With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20 - 25℃; for 1.5h; 2.2-A [Example 2]; (9S)-9-Ethyl-9-(glycyl-sarcosyloxy)-1-pentyl-1H,12H-pyrano[3",4":6',7']indolizino[1',2':6,5]pyrido[4,3,2-de]quinazoline-10,13(9H,15H)-dione hydrochloride (compound 2A); [Show Image] Process 2-A; (9S)-9-[N-(tert-Butoxycarbonyl)-glycyl]-sarcosyloxy}-9-ethyl-1-pentyl-1H,12H-pyrano[3",4": 6',7']indolizino[1',2':6,5]pyrido[4,3,2-de]quinazoline-10,13(9H,15H)-dione; [Show Image] 1.4 g (5.67 mmol) of [N-(tert-butoxycarbonyl)-glycyl]-sarcosine, which is a known substance (Helvetica Chimica Acta, 1991, 74, 197), 1.3 g (2.84 mmol) of (9S)-9-ethyl-9-hydroxy-1-pentyl-1H,12H-pyrano[3",4":6',7']indolizino[1',2':6,5]pyrido[4,3,2-d e]quinazoline-10,13(9H,15H)-dione, 2.2 g (11.34 mmol) of 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride, and 1.4 g (11.34 mmol) of 4-dimethylaminopyridine were dissolved in methylene chloride (50 mL), and then stirred at room temperature for 1.5 hours. The reaction solution was washed with 0.2 N aqueous hydrochloric acid and saturated aqueous sodium hydrogen carbonate solution, then dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. Purification of the resulting residue was performed using silica gel column chromatography (methylene chloride:methanol = 100:1 to 30:1), and as a result, 1.34 g (69%) of (9S)-9-[N-(tert-butoxycarbonyl)-glycyl]-sarcosyloxy}-9-ethyl-1-pentyl-1H,12H-pyrano[3",4":6 ',7']indolizino[1',2':6,5]pyrido[4,3,2-de]quinazoline-10,13(9H,15H)-dione was obtained as a yellowish red amorphous substance. 1H-NMR (270MHz, CDCl3) δ(ppm): Rotamer A* 0.86-1.04 (6H, m), 1.24-1.53 (4H, m), 1.38 (9H, s), 1.70-1.90 (2H, m), 2.03-2.36 (2H, m), 3.04 (3H, s), 3.83 (2H, t, J = 7.1 Hz), 3.96-4.05 (2H, m), 4.12 (1H, d, J = 17.7 Hz), 4.57 (1H, d, J = 17.7 Hz), 5.21 (2H, s), 5.38 (1H, d, J = 17.3 Hz), 5.46-5.56 (1H, m), 5.66 (1H, d, J = 17.3 Hz), 7.10-7.21 (2H, m), 7.40 (1H, s), 7.60-7.75 (2H, m); Rotamer B* 0.86-1.04 (6H, m), 1.24-1.53 (4H, m), 1.38 (9H, s), 1.70-1.90 (2H, m), 2.03-2.36 (2H, m), 3.02 (3H, s), 3.83 (2H, t, J = 7.1 Hz), 3.90-3.96 (2H, m), 4.12 (1H, d, J = 17.7 Hz), 4.57 (1H, d, J = 17.7 Hz), 5.24 (2H, s), 5.38 (1H, d, J = 17.3 Hz), 5.46-5.56 (1H, m), 5.68 (1H, d, J = 17.3 Hz), 7.10-7.21 (2H, m), 7.40 (1H, s), 7.60-7.75 (2H, m). *The ratio of the two rotamers, A and B, was approximately 5:1. ESI (LC-MS positive mode) m/z 687 (M+H).
69% With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 1.5h; 2.A Process 2-A (9S)-9-[N-(tert-Butoxycarbonyl)-glycyl]-sarcosyloxy}-9-ethyl-1-pentyl-1H,12H-pyrano[3",4": 6',7']indolizino[1',2':6,5]pyrido[4,3,2-de]quinazoline-10,13(9H,15H)-dione; [Show Image] 1.4 g (5.67 mmol) of [N-(tert-butoxycarbonyl)-glycyl]-sarcosine, which is a known substance (Helvetica Chimica Acta, 1991, 74, 197), 1.3 g (2.84 mmol) of (9S)-9-ethyl-9-hydroxy-1-pentyl-1H,12H-pyrano[3",4":6',7']indolizino[1',2':6,5]pyrido[4,3,2-d e]quinazoline-10,13(9H,15H)-dione, 2.2 g (11.34 mmol) of 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride, and 1.4 g (11.34 mmol) of 4-dimethylaminopyridine were dissolved in methylene chloride (50 mL), and then stirred at room temperature for 1.5 hours. The reaction solution was washed with 0.2 N aqueous hydrochloric acid and saturated aqueous sodium hydrogen carbonate solution, then dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. Purification of the resulting residue was performed using silica gel column chromatography (methylene chloride:methanol = 100:1 to 30:1), and as a result, 1.34 g (69%) of (9S)-9-[N-(tert-butoxycarbonyl)-glycyl]-sarcosyloxy}-9-ethyl-1-pentyl-1H,12H-pyrano[3",4":6 ',7']indolizino[1',2':6,5]pyrido[4,3,2-de]quinazoline-10,13(9H,15H)-dione was obtained as a yellowish red amorphous substance. 1H-NMR (270MHz, CDCl3) δ(ppm): Rotamer A* 0.86-1.04 (6H, m), 1.24-1.53 (4H, m), 1.38 (9H, s), 1.70-1.90 (2H, m), 2.03-2.36 (2H, m), 3.04 (3H, s), 3.83 (2H, t, J = 7.1 Hz), 3.96-4.05 (2H, m), 4.12 (1H, d, J = 17.7 Hz), 4.57 (1H, d, J = 17.7 Hz), 5.21 (2H, s), 5.38 (1H, d, J = 17.3 Hz), 5.46-5.56 (1H, m), 5.66 (1H, d, J = 17.3 Hz), 7.10-7.21 (2H, m), 7.40 (1H, s), 7.60-7.75 (2H, m); Rotamer B* 0.86-1.04 (6H, m), 1.24-1.53 (4H, m), 1.38 (9H, s), 1.70-1.90 (2H, m), 2.03-2.36 (2H, m), 3.02 (3H, s), 3.83 (2H, t, J = 7.1 Hz), 3.90-3.96 (2H, m), 4.12 (1H, d, J = 17.7 Hz), 4.57 (1H, d, J = 17.7 Hz), 5.24 (2H, s), 5.38 (1H, d, J = 17.3 Hz), 5.46-5.56 (1H, m), 5.68 (1H, d, J = 17.3 Hz), 7.10-7.21 (2H, m), 7.40 (1H, s), 7.60-7.75 (2H, m). *The ratio of the two rotamers, A and B, was approximately 5:1. ESI (LC-MS positive mode) m/z 687 (M+H).
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 1h;

  • 30
  • [ 133498-97-2 ]
  • [ 1515605-42-1 ]
  • [ 1515606-22-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere 2.1: hydrogenchloride / ethyl acetate / 0.5 h / 20 °C / Inert atmosphere 3.1: acetic anhydride / 1 h / 55 °C / Inert atmosphere 3.2: 0.5 h / 0 - 20 °C / Inert atmosphere 4.1: triethylamine; bis(trichloromethyl) carbonate / dichloromethane / 0.5 h / -78 °C / Inert atmosphere 5.1: triethylphosphine / toluene / 48 h / 70 °C / Inert atmosphere
  • 31
  • [ 133498-97-2 ]
  • [ 1515605-80-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere 2.1: hydrogenchloride / ethyl acetate / 0.5 h / 20 °C / Inert atmosphere 3.1: acetic anhydride / 1 h / 55 °C / Inert atmosphere 3.2: 0.5 h / 0 - 20 °C / Inert atmosphere 4.1: triethylamine; bis(trichloromethyl) carbonate / dichloromethane / 0.5 h / -78 °C / Inert atmosphere 5.1: triethylphosphine / toluene / 48 h / 70 °C / Inert atmosphere 6.1: triethylamine tris(hydrogen fluoride) / acetonitrile / 19 h / 50 °C / Inert atmosphere
  • 32
  • [ 133498-97-2 ]
  • [ 1515605-84-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere 2.1: hydrogenchloride / ethyl acetate / 0.5 h / 20 °C / Inert atmosphere 3.1: acetic anhydride / 1 h / 55 °C / Inert atmosphere 3.2: 0.5 h / 0 - 20 °C / Inert atmosphere 4.1: triethylamine; bis(trichloromethyl) carbonate / dichloromethane / 0.5 h / -78 °C / Inert atmosphere 5.1: triethylphosphine / toluene / 48 h / 70 °C / Inert atmosphere 6.1: dmap; triethylamine / acetonitrile / 12 h / 20 °C / Inert atmosphere 7.1: tri-n-butyl-tin hydride; 2,2'-azobis(isobutyronitrile) / 2,2,2-trifluoroethanol / 1 h / 78 °C / Inert atmosphere
  • 33
  • [ 133498-97-2 ]
  • [ 1515605-90-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere 2.1: hydrogenchloride / ethyl acetate / 0.5 h / 20 °C / Inert atmosphere 3.1: acetic anhydride / 1 h / 55 °C / Inert atmosphere 3.2: 0.5 h / 0 - 20 °C / Inert atmosphere 4.1: triethylamine; bis(trichloromethyl) carbonate / dichloromethane / 0.5 h / -78 °C / Inert atmosphere 5.1: triethylphosphine / toluene / 48 h / 70 °C / Inert atmosphere 6.1: dmap; triethylamine / acetonitrile / 12 h / 20 °C / Inert atmosphere 7.1: tri-n-butyl-tin hydride; 2,2'-azobis(isobutyronitrile) / 2,2,2-trifluoroethanol / 1 h / 78 °C / Inert atmosphere 8.1: morpholine; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere
  • 34
  • [ 133498-97-2 ]
  • [ 1515605-92-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 9 steps 1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere 2.1: hydrogenchloride / ethyl acetate / 0.5 h / 20 °C / Inert atmosphere 3.1: acetic anhydride / 1 h / 55 °C / Inert atmosphere 3.2: 0.5 h / 0 - 20 °C / Inert atmosphere 4.1: triethylamine; bis(trichloromethyl) carbonate / dichloromethane / 0.5 h / -78 °C / Inert atmosphere 5.1: triethylphosphine / toluene / 48 h / 70 °C / Inert atmosphere 6.1: dmap; triethylamine / acetonitrile / 12 h / 20 °C / Inert atmosphere 7.1: tri-n-butyl-tin hydride; 2,2'-azobis(isobutyronitrile) / 2,2,2-trifluoroethanol / 1 h / 78 °C / Inert atmosphere 8.1: morpholine; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere 9.1: sodium hydrogencarbonate; 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one / N,N-dimethyl-formamide; dichloromethane / 24 h / 0 - 20 °C / Inert atmosphere
Multi-step reaction with 9 steps 1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere 2.1: hydrogenchloride / ethyl acetate / 0.5 h / 20 °C / Inert atmosphere 3.1: acetic anhydride / 1 h / 55 °C / Inert atmosphere 3.2: 0.5 h / 0 - 20 °C / Inert atmosphere 4.1: triethylamine; bis(trichloromethyl) carbonate / dichloromethane / 0.5 h / -78 °C / Inert atmosphere 5.1: triethylphosphine / toluene / 48 h / 70 °C / Inert atmosphere 6.1: dmap; triethylamine / acetonitrile / 12 h / 20 °C / Inert atmosphere 7.1: tri-n-butyl-tin hydride; 2,2'-azobis(isobutyronitrile) / 2,2,2-trifluoroethanol / 1 h / 78 °C / Inert atmosphere 8.1: hydrogenchloride / 1,4-dioxane / 0.5 h / 20 °C / Inert atmosphere 9.1: sodium hydrogencarbonate; 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one / N,N-dimethyl-formamide; dichloromethane / 24 h / 0 - 20 °C / Inert atmosphere
  • 35
  • [ 133498-97-2 ]
  • [ 1515605-40-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 11 steps 1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere 2.1: hydrogenchloride / ethyl acetate / 0.5 h / 20 °C / Inert atmosphere 3.1: acetic anhydride / 1 h / 55 °C / Inert atmosphere 3.2: 0.5 h / 0 - 20 °C / Inert atmosphere 4.1: triethylamine; bis(trichloromethyl) carbonate / dichloromethane / 0.5 h / -78 °C / Inert atmosphere 5.1: triethylphosphine / toluene / 48 h / 70 °C / Inert atmosphere 6.1: dmap; triethylamine / acetonitrile / 12 h / 20 °C / Inert atmosphere 7.1: tri-n-butyl-tin hydride; 2,2'-azobis(isobutyronitrile) / 2,2,2-trifluoroethanol / 1 h / 78 °C / Inert atmosphere 8.1: hydrogenchloride / 1,4-dioxane / 0.5 h / 20 °C / Inert atmosphere 9.1: sodium hydrogencarbonate; 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one / N,N-dimethyl-formamide; dichloromethane / 24 h / 0 - 20 °C / Inert atmosphere 10.1: hydrogenchloride / 1,4-dioxane / 0.5 h / Inert atmosphere 11.1: sodium hydrogencarbonate; 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one / N,N-dimethyl-formamide; dichloromethane / 48 h / 0 - 20 °C / Inert atmosphere
Multi-step reaction with 11 steps 1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere 2.1: hydrogenchloride / ethyl acetate / 0.5 h / 20 °C / Inert atmosphere 3.1: acetic anhydride / 1 h / 55 °C / Inert atmosphere 3.2: 0.5 h / 0 - 20 °C / Inert atmosphere 4.1: triethylamine; bis(trichloromethyl) carbonate / dichloromethane / 0.5 h / -78 °C / Inert atmosphere 5.1: triethylphosphine / toluene / 48 h / 70 °C / Inert atmosphere 6.1: dmap; triethylamine / acetonitrile / 12 h / 20 °C / Inert atmosphere 7.1: tri-n-butyl-tin hydride; 2,2'-azobis(isobutyronitrile) / 2,2,2-trifluoroethanol / 1 h / 78 °C / Inert atmosphere 8.1: morpholine; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere 9.1: sodium hydrogencarbonate; 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one / N,N-dimethyl-formamide; dichloromethane / 24 h / 0 - 20 °C / Inert atmosphere 10.1: hydrogenchloride / 1,4-dioxane / 0.5 h / Inert atmosphere 11.1: sodium hydrogencarbonate; 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one / N,N-dimethyl-formamide; dichloromethane / 48 h / 0 - 20 °C / Inert atmosphere
  • 36
  • [ 133498-97-2 ]
  • (-)-sandramycin [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 13 steps 1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere 2.1: hydrogenchloride / ethyl acetate / 0.5 h / 20 °C / Inert atmosphere 3.1: acetic anhydride / 1 h / 55 °C / Inert atmosphere 3.2: 0.5 h / 0 - 20 °C / Inert atmosphere 4.1: triethylamine; bis(trichloromethyl) carbonate / dichloromethane / 0.5 h / -78 °C / Inert atmosphere 5.1: triethylphosphine / toluene / 48 h / 70 °C / Inert atmosphere 6.1: dmap; triethylamine / acetonitrile / 12 h / 20 °C / Inert atmosphere 7.1: tri-n-butyl-tin hydride; 2,2'-azobis(isobutyronitrile) / 2,2,2-trifluoroethanol / 1 h / 78 °C / Inert atmosphere 8.1: hydrogenchloride / 1,4-dioxane / 0.5 h / 20 °C / Inert atmosphere 9.1: sodium hydrogencarbonate; 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one / N,N-dimethyl-formamide; dichloromethane / 24 h / 0 - 20 °C / Inert atmosphere 10.1: hydrogenchloride / 1,4-dioxane / 0.5 h / Inert atmosphere 11.1: sodium hydrogencarbonate; 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one / N,N-dimethyl-formamide; dichloromethane / 48 h / 0 - 20 °C / Inert atmosphere 12.1: 10% palladium hydroxide on charcoal; hydrogen / methanol / 3 h / 20 °C 13.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 24 h / 0 - 20 °C / Inert atmosphere
Multi-step reaction with 13 steps 1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere 2.1: hydrogenchloride / ethyl acetate / 0.5 h / 20 °C / Inert atmosphere 3.1: acetic anhydride / 1 h / 55 °C / Inert atmosphere 3.2: 0.5 h / 0 - 20 °C / Inert atmosphere 4.1: triethylamine; bis(trichloromethyl) carbonate / dichloromethane / 0.5 h / -78 °C / Inert atmosphere 5.1: triethylphosphine / toluene / 48 h / 70 °C / Inert atmosphere 6.1: dmap; triethylamine / acetonitrile / 12 h / 20 °C / Inert atmosphere 7.1: tri-n-butyl-tin hydride; 2,2'-azobis(isobutyronitrile) / 2,2,2-trifluoroethanol / 1 h / 78 °C / Inert atmosphere 8.1: morpholine; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere 9.1: sodium hydrogencarbonate; 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one / N,N-dimethyl-formamide; dichloromethane / 24 h / 0 - 20 °C / Inert atmosphere 10.1: hydrogenchloride / 1,4-dioxane / 0.5 h / Inert atmosphere 11.1: sodium hydrogencarbonate; 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one / N,N-dimethyl-formamide; dichloromethane / 48 h / 0 - 20 °C / Inert atmosphere 12.1: 10% palladium hydroxide on charcoal; hydrogen / methanol / 3 h / 20 °C 13.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 24 h / 0 - 20 °C / Inert atmosphere
  • 37
  • [ 133498-97-2 ]
  • [ 1515606-23-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere 2.1: hydrogenchloride / ethyl acetate / 0.5 h / 20 °C / Inert atmosphere 3.1: acetic anhydride / 1 h / 55 °C / Inert atmosphere 3.2: 0.5 h / 0 - 20 °C / Inert atmosphere 4.1: triethylamine; bis(trichloromethyl) carbonate / dichloromethane / 0.5 h / -78 °C / Inert atmosphere 5.1: triethylphosphine / toluene / 48 h / 70 °C / Inert atmosphere 6.1: trifluoroacetic acid / dichloromethane / 2.5 h / 0 °C / Inert atmosphere
  • 38
  • [ 133498-97-2 ]
  • [ 1515606-24-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere 2.1: hydrogenchloride / ethyl acetate / 0.5 h / 20 °C / Inert atmosphere 3.1: acetic anhydride / 1 h / 55 °C / Inert atmosphere 3.2: 0.5 h / 0 - 20 °C / Inert atmosphere 4.1: triethylamine; bis(trichloromethyl) carbonate / dichloromethane / 0.5 h / -78 °C / Inert atmosphere 5.1: triethylphosphine / toluene / 48 h / 70 °C / Inert atmosphere 6.1: morpholine; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere
  • 39
  • [ 133498-97-2 ]
  • [ 1515605-59-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere 2.1: hydrogenchloride / ethyl acetate / 0.5 h / 20 °C / Inert atmosphere 3.1: acetic anhydride / 1 h / 55 °C / Inert atmosphere 3.2: 0.5 h / 0 - 20 °C / Inert atmosphere
  • 40
  • [ 133498-97-2 ]
  • [ 1515606-17-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere 2: hydrogenchloride / ethyl acetate / 0.5 h / 20 °C / Inert atmosphere
  • 41
  • [ 133498-97-2 ]
  • [ 1515605-46-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere 2.1: hydrogenchloride / ethyl acetate / 0.5 h / 20 °C / Inert atmosphere 3.1: acetic anhydride / 1 h / 55 °C / Inert atmosphere 3.2: 0.5 h / 0 - 20 °C / Inert atmosphere 4.1: triethylamine; bis(trichloromethyl) carbonate / dichloromethane / 0.5 h / -78 °C / Inert atmosphere
  • 42
  • [ 133498-97-2 ]
  • [ 1515605-81-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere 2.1: hydrogenchloride / ethyl acetate / 0.5 h / 20 °C / Inert atmosphere 3.1: acetic anhydride / 1 h / 55 °C / Inert atmosphere 3.2: 0.5 h / 0 - 20 °C / Inert atmosphere 4.1: triethylamine; bis(trichloromethyl) carbonate / dichloromethane / 0.5 h / -78 °C / Inert atmosphere 5.1: triethylphosphine / toluene / 48 h / 70 °C / Inert atmosphere 6.1: dmap; triethylamine / acetonitrile / 12 h / 20 °C / Inert atmosphere
  • 43
  • [ 133498-97-2 ]
  • [ 1515605-87-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere 2.1: hydrogenchloride / ethyl acetate / 0.5 h / 20 °C / Inert atmosphere 3.1: acetic anhydride / 1 h / 55 °C / Inert atmosphere 3.2: 0.5 h / 0 - 20 °C / Inert atmosphere 4.1: triethylamine; bis(trichloromethyl) carbonate / dichloromethane / 0.5 h / -78 °C / Inert atmosphere 5.1: triethylphosphine / toluene / 48 h / 70 °C / Inert atmosphere 6.1: dmap; triethylamine / acetonitrile / 12 h / 20 °C / Inert atmosphere 7.1: tri-n-butyl-tin hydride; 2,2'-azobis(isobutyronitrile) / 2,2,2-trifluoroethanol / 1 h / 78 °C / Inert atmosphere 8.1: hydrogenchloride / 1,4-dioxane / 0.5 h / 20 °C / Inert atmosphere
  • 44
  • [ 133498-97-2 ]
  • [ 1574776-16-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 10 steps 1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere 2.1: hydrogenchloride / ethyl acetate / 0.5 h / 20 °C / Inert atmosphere 3.1: acetic anhydride / 1 h / 55 °C / Inert atmosphere 3.2: 0.5 h / 0 - 20 °C / Inert atmosphere 4.1: triethylamine; bis(trichloromethyl) carbonate / dichloromethane / 0.5 h / -78 °C / Inert atmosphere 5.1: triethylphosphine / toluene / 48 h / 70 °C / Inert atmosphere 6.1: dmap; triethylamine / acetonitrile / 12 h / 20 °C / Inert atmosphere 7.1: tri-n-butyl-tin hydride; 2,2'-azobis(isobutyronitrile) / 2,2,2-trifluoroethanol / 1 h / 78 °C / Inert atmosphere 8.1: morpholine; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere 9.1: sodium hydrogencarbonate; 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one / N,N-dimethyl-formamide; dichloromethane / 24 h / 0 - 20 °C / Inert atmosphere 10.1: morpholine; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere
Multi-step reaction with 10 steps 1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere 2.1: hydrogenchloride / ethyl acetate / 0.5 h / 20 °C / Inert atmosphere 3.1: acetic anhydride / 1 h / 55 °C / Inert atmosphere 3.2: 0.5 h / 0 - 20 °C / Inert atmosphere 4.1: triethylamine; bis(trichloromethyl) carbonate / dichloromethane / 0.5 h / -78 °C / Inert atmosphere 5.1: triethylphosphine / toluene / 48 h / 70 °C / Inert atmosphere 6.1: dmap; triethylamine / acetonitrile / 12 h / 20 °C / Inert atmosphere 7.1: tri-n-butyl-tin hydride; 2,2'-azobis(isobutyronitrile) / 2,2,2-trifluoroethanol / 1 h / 78 °C / Inert atmosphere 8.1: hydrogenchloride / 1,4-dioxane / 0.5 h / 20 °C / Inert atmosphere 9.1: sodium hydrogencarbonate; 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one / N,N-dimethyl-formamide; dichloromethane / 24 h / 0 - 20 °C / Inert atmosphere 10.1: morpholine; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere
  • 45
  • [ 133498-97-2 ]
  • [ 1515606-29-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 10 steps 1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere 2.1: hydrogenchloride / ethyl acetate / 0.5 h / 20 °C / Inert atmosphere 3.1: acetic anhydride / 1 h / 55 °C / Inert atmosphere 3.2: 0.5 h / 0 - 20 °C / Inert atmosphere 4.1: triethylamine; bis(trichloromethyl) carbonate / dichloromethane / 0.5 h / -78 °C / Inert atmosphere 5.1: triethylphosphine / toluene / 48 h / 70 °C / Inert atmosphere 6.1: dmap; triethylamine / acetonitrile / 12 h / 20 °C / Inert atmosphere 7.1: tri-n-butyl-tin hydride; 2,2'-azobis(isobutyronitrile) / 2,2,2-trifluoroethanol / 1 h / 78 °C / Inert atmosphere 8.1: hydrogenchloride / 1,4-dioxane / 0.5 h / 20 °C / Inert atmosphere 9.1: sodium hydrogencarbonate; 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one / N,N-dimethyl-formamide; dichloromethane / 24 h / 0 - 20 °C / Inert atmosphere 10.1: hydrogenchloride / 1,4-dioxane / 0.5 h / Inert atmosphere
Multi-step reaction with 10 steps 1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere 2.1: hydrogenchloride / ethyl acetate / 0.5 h / 20 °C / Inert atmosphere 3.1: acetic anhydride / 1 h / 55 °C / Inert atmosphere 3.2: 0.5 h / 0 - 20 °C / Inert atmosphere 4.1: triethylamine; bis(trichloromethyl) carbonate / dichloromethane / 0.5 h / -78 °C / Inert atmosphere 5.1: triethylphosphine / toluene / 48 h / 70 °C / Inert atmosphere 6.1: dmap; triethylamine / acetonitrile / 12 h / 20 °C / Inert atmosphere 7.1: tri-n-butyl-tin hydride; 2,2'-azobis(isobutyronitrile) / 2,2,2-trifluoroethanol / 1 h / 78 °C / Inert atmosphere 8.1: morpholine; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere 9.1: sodium hydrogencarbonate; 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one / N,N-dimethyl-formamide; dichloromethane / 24 h / 0 - 20 °C / Inert atmosphere 10.1: hydrogenchloride / 1,4-dioxane / 0.5 h / Inert atmosphere
  • 46
  • [ 133498-97-2 ]
  • (3R,7S,16S,23R,27S,36S)-3,23-Diamino-7,27-diisopropyl-8,11,28,31-tetramethyl-5,25-dioxa-1,8,11,14,21,28,31,34-octaaza-tricyclo[34.4.0.016,21]tetracontane-2,6,9,12,15,22,26,29,32,35-decaone [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 12 steps 1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere 2.1: hydrogenchloride / ethyl acetate / 0.5 h / 20 °C / Inert atmosphere 3.1: acetic anhydride / 1 h / 55 °C / Inert atmosphere 3.2: 0.5 h / 0 - 20 °C / Inert atmosphere 4.1: triethylamine; bis(trichloromethyl) carbonate / dichloromethane / 0.5 h / -78 °C / Inert atmosphere 5.1: triethylphosphine / toluene / 48 h / 70 °C / Inert atmosphere 6.1: dmap; triethylamine / acetonitrile / 12 h / 20 °C / Inert atmosphere 7.1: tri-n-butyl-tin hydride; 2,2'-azobis(isobutyronitrile) / 2,2,2-trifluoroethanol / 1 h / 78 °C / Inert atmosphere 8.1: hydrogenchloride / 1,4-dioxane / 0.5 h / 20 °C / Inert atmosphere 9.1: sodium hydrogencarbonate; 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one / N,N-dimethyl-formamide; dichloromethane / 24 h / 0 - 20 °C / Inert atmosphere 10.1: hydrogenchloride / 1,4-dioxane / 0.5 h / Inert atmosphere 11.1: sodium hydrogencarbonate; 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one / N,N-dimethyl-formamide; dichloromethane / 48 h / 0 - 20 °C / Inert atmosphere 12.1: 10% palladium hydroxide on charcoal; hydrogen / methanol / 3 h / 20 °C
Multi-step reaction with 12 steps 1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere 2.1: hydrogenchloride / ethyl acetate / 0.5 h / 20 °C / Inert atmosphere 3.1: acetic anhydride / 1 h / 55 °C / Inert atmosphere 3.2: 0.5 h / 0 - 20 °C / Inert atmosphere 4.1: triethylamine; bis(trichloromethyl) carbonate / dichloromethane / 0.5 h / -78 °C / Inert atmosphere 5.1: triethylphosphine / toluene / 48 h / 70 °C / Inert atmosphere 6.1: dmap; triethylamine / acetonitrile / 12 h / 20 °C / Inert atmosphere 7.1: tri-n-butyl-tin hydride; 2,2'-azobis(isobutyronitrile) / 2,2,2-trifluoroethanol / 1 h / 78 °C / Inert atmosphere 8.1: morpholine; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere 9.1: sodium hydrogencarbonate; 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one / N,N-dimethyl-formamide; dichloromethane / 24 h / 0 - 20 °C / Inert atmosphere 10.1: hydrogenchloride / 1,4-dioxane / 0.5 h / Inert atmosphere 11.1: sodium hydrogencarbonate; 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one / N,N-dimethyl-formamide; dichloromethane / 48 h / 0 - 20 °C / Inert atmosphere 12.1: 10% palladium hydroxide on charcoal; hydrogen / methanol / 3 h / 20 °C
  • 47
  • [ 133498-97-2 ]
  • [ 107-18-6 ]
  • [ 1515605-55-6 ]
YieldReaction ConditionsOperation in experiment
2.6 g With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; for 3h; Inert atmosphere;
  • 48
  • [ 29816-01-1 ]
  • [ 24424-99-5 ]
  • [ 133498-97-2 ]
  • 49
  • [ 534605-78-2 ]
  • [ 133498-97-2 ]
  • TP300 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 1.5 h / 20 °C 2: hydrogenchloride; acetic acid / 2.75 h / 20 °C
  • 50
  • [ 133498-97-2 ]
  • [ 7689-03-4 ]
  • (aminoacetyl-methyl-amino)-acetic acid (S)-4-ethyl-3,13-dioxo-3,4,12,13-tetrahydro-1H-2-oxa-6,12a-diaza-dibenzo[b,h]fluoren-4-yl ester hydrochloric acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 15 h / 20 °C 2: hydrogenchloride / ethyl acetate / 4 h / 20 °C
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