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[ CAS No. 114873-13-1 ] {[proInfo.proName]}

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Chemical Structure| 114873-13-1
Chemical Structure| 114873-13-1
Structure of 114873-13-1 * Storage: {[proInfo.prStorage]}
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Product Details of [ 114873-13-1 ]

CAS No. :114873-13-1 MDL No. :MFCD00151887
Formula : C14H17Cl2NO4 Boiling Point : -
Linear Structure Formula :- InChI Key :UGZIQCCPEDCGGN-LLVKDONJSA-N
M.W : 334.20 Pubchem ID :7015811
Synonyms :

Calculated chemistry of [ 114873-13-1 ]

Physicochemical Properties

Num. heavy atoms : 21
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.43
Num. rotatable bonds : 7
Num. H-bond acceptors : 4.0
Num. H-bond donors : 2.0
Molar Refractivity : 81.36
TPSA : 75.63 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.66 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.51
Log Po/w (XLOGP3) : 3.77
Log Po/w (WLOGP) : 3.51
Log Po/w (MLOGP) : 3.01
Log Po/w (SILICOS-IT) : 2.97
Consensus Log Po/w : 3.15

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.04
Solubility : 0.0307 mg/ml ; 0.0000919 mol/l
Class : Moderately soluble
Log S (Ali) : -5.05
Solubility : 0.00297 mg/ml ; 0.00000888 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -4.38
Solubility : 0.014 mg/ml ; 0.0000418 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.83

Safety of [ 114873-13-1 ]

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

Application In Synthesis of [ 114873-13-1 ]

* 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 [ 114873-13-1 ]

[ 114873-13-1 ] Synthesis Path-Downstream   1~26

  • 2
  • [ 13734-34-4 ]
  • [ CAS Unavailable ]
  • [ 5241-64-5 ]
  • [ 114873-13-1 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multistep reaction;
  • 3
  • [ 114873-13-1 ]
  • [ 710280-85-6 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
97% With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In N,N-dimethyl-formamide at 20℃; for 20h;
  • 4
  • [ CAS Unavailable ]
  • [ 114873-13-1 ]
  • [ 521098-38-4 ]
YieldReaction ConditionsOperation in experiment
With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane
  • 5
  • [ 114873-13-1 ]
  • [ 74-88-4 ]
  • [ 583028-43-7 ]
YieldReaction ConditionsOperation in experiment
93% With acetic acid; silver(l) oxide In N,N-dimethyl-formamide at 20℃; for 20h;
  • 6
  • [ 114873-13-1 ]
  • [ CAS Unavailable ]
  • [ 654068-60-7 ]
YieldReaction ConditionsOperation in experiment
1.00 g With benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide In tetrahydrofuran at 0 - 20℃; for 16.5h;
  • 8
  • [ 114873-13-1 ]
  • [ 479585-72-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: Et3N / tetrahydrofuran 2: diethyl ether 3: aq. C6H5CO2Ag / dioxane / 20 °C / sonication 4: 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide; HOBT; DIEA / dimethylformamide 5: CF3CO2H / CH2Cl2
  • 10
  • N-Boc-D-3,4-dichlorophenylalanine [ No CAS ]
  • [ 269396-56-7 ]
  • 11
  • [ 114873-13-1 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: Et3N / tetrahydrofuran 2: diethyl ether 3: aq. C6H5CO2Ag / dioxane / 20 °C / sonication 4: 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide; HOBT; DIEA / dimethylformamide
  • 14
  • [ 114873-13-1 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: DIPCDI; HOAt; DIEA / dimethylformamide 2: TFA / CH2Cl2 3: Et3N / methanol / Heating 4: NaH / dimethylformamide 5: TFA / CH2Cl2
  • 16
  • [ 114873-13-1 ]
  • [ 204690-90-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: DIPCDI; HOAt; DIEA / dimethylformamide 2: TFA / CH2Cl2 3: Et3N / methanol / Heating 4: NaH / dimethylformamide 5: TFA / CH2Cl2 6: HATU; HOAt; DIEA / dimethylformamide 7: TFA
  • 17
  • [ 114873-13-1 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: DIPCDI; HOAt; DIEA / dimethylformamide 2: TFA / CH2Cl2 3: Et3N / methanol / Heating 4: NaH / dimethylformamide 5: TFA / CH2Cl2 6: HATU; HOAt; DIEA / dimethylformamide
  • 18
  • [ 10462-00-7 ]
  • [ 114873-13-1 ]
  • [ 1225591-35-4 ]
YieldReaction ConditionsOperation in experiment
26% With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 2h; 5.5-1 Example 5: Ethyl 4-cyclohexyl-1-((R)-3-(3,4-dichlorophenyl)-2-{3-[2-(1 H- imidazol-4-yl)ethyl]ureido}propionyl)piperidine-4-carboxylate:5-1 Ethyl 1-[(R)-2-tert-butoxycarbonylamino-3-(3,4-dichlorophenyl)propionyl]-4- cyclohexylpiperidine^-carboxylate0.5 g (2.1 mmol) of ethyl pipehdine-4-cyclohexyl-4'-carboxylate (cf. preparation 4-1- 2), 0.7 g (2.1 mmol) of (R)-2-tert-butoxycarbonylamino-3-(3,4-dichlorophenyl)- propionic, 0.31 g (2.3 mmol) of HOBT, 0.44 g (2.3 mmol) of EDC and 0.73 ml (4.2 mmol) of diisopropylethylamine are placed in 5 ml of DMF. The mixture is stirred for 2 hours at room temperature. The reaction is stopped by addition of an aqueous 5% citric acid solution. The organic compounds are extracted with ethyl acetate, then the organic phase is washed with aqueous 1 N sodium hydroxide solution and then with water. The organic phase is dried over sodium sulfate, filtered and concentrated. The oil obtained is chromatographed on silica gel (eluent: 1/1 heptane/ethyl acetate). 300 mg of ethyl 1 -[(R)-2-tert-butoxycarbonylamino-3-(3,4-dichlorophenyl)propionyl]-4- cyclohexylpiperidine-4-carboxylate are obtained in a yield of 26%. 1H NMR CDCh: results given in figure 4 (mixture of conformers)
26% With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 2h; 21.1 21-1 Ethyl 1-[(R)-2-tert-butoxycarbonylamino-3-(3, 4-dichlorophenyl)propionyl]-4- cyclohexylpiperidine-4-carboxylate; 0.5 g (2.1 mmol) of ethyl piperidine-4-cyclohexyl-4'-carboxylate (cf. preparation 3-1 - 2), 0.7 g (2.1 mmol) of Boc-3,4-dichloro-D-phenylalanine, 0.31 g (2.3 mmol) of HOBT, 0.44 g (2.3 mmol) of EDC and 0.73 ml. (4.2 mmol) of diisopropylethylamine are placed in 5 ml_ of dimethylformamide. The mixture is stirred for 2 hours at room temperature and then washed with aqueous 5% citric acid solution and extracted with ethyl acetate. The organic phase is washed with aqueous 1 N sodium hydroxide solution and then with water and dried over sodium sulfate, filtered and finally concentrated to dryness. The oil obtained is chromatographed (eluent: 5/5 heptane/ethyl acetate). 300 mg of ethyl 1 -[(R)-2-tert-butoxycarbonylamino-3-(3,4- dichlorophenyl)propionyl]-4-cyclohexylpiperidine-4-carboxylate are obtained in a yield of 26%.
  • 20
  • [ CAS Unavailable ]
  • [ 114873-13-1 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
28% With dmap; 2,2'-dipyridyl carbonate In toluene at 78℃; for 10h; Inert atmosphere;
  • 22
  • [ 24424-99-5 ]
  • [ CAS Unavailable ]
  • [ 114873-13-1 ]
YieldReaction ConditionsOperation in experiment
100% With sodium hydroxide In 1,4-dioxane; water at 20℃; 123.1 Step 1: (2R)-2-(tert-butoxycarbonylamino)-3-(3,4-dichlorophenyl)propanoic acid In a round-bottomed flask, to a stirred solution of 3,4-dichloro-D-phenylalanine (96%, 600 mg, 2.46 mmol) in 1,4-dioxane (9.8361 mL) and water (4.918 mL) at 0 °C were added successively 1 M NaOH (4.9 mL, 4.92 mmol) and di-tert-butyl dicarbonate (591 mg, 2.71 mmol) slowly. The mixture was stirred overnight at room temperature. Ethyl acetate was added, the mixture was cooled to 0 °C and acidified to pH = 3 with 1.0 M KHSO4. Layers were separated and the aqueous layer was extracted twice more with ethyl acetate. The combined organic layers were dried over Na2SO4and concentrated in vacuo to afford the title compound as a white solid (1.04 g, 100% yield, tr = 0.89 min). LCMS (Method F): m/z found 234.1 [M+H-Boc]+;1H-NMR (DMSO-d6, 400 MHz): δ (ppm) 12.65 (s, 1H), 7.60 - 7.48 (m, 2H), 7.26 (dd, J=8.3, 1.9 Hz, 1H), 7.19 - 6.70 (m, 1H), 4.12 (td, J=10.5, 4.5 Hz, 1H), 3.05 (dd, J=13.8, 4.4 Hz, 1H), 2.82 (dd, J=13.7, 10.8 Hz, 1H), 1.32 (s, 9H).
  • 23
  • [ 114873-13-1 ]
  • [ 2819659-44-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: HATU; N-ethyl-N,N-diisopropylamine / 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran / 10 min / 20 °C / Inert atmosphere; Sealed tube 1.2: 20 °C 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / 0 - 20 °C / Inert atmosphere
  • 24
  • [ 114873-13-1 ]
  • [ 2819659-45-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: HATU; N-ethyl-N,N-diisopropylamine / 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran / 10 min / 20 °C / Inert atmosphere; Sealed tube 1.2: 20 °C 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / 0 - 20 °C / Inert atmosphere 3.1: hydrogenchloride / 1,4-dioxane / 20 °C
  • 25
  • [ 114873-13-1 ]
  • [ 2819658-87-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: HATU; N-ethyl-N,N-diisopropylamine / 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran / 10 min / 20 °C / Inert atmosphere; Sealed tube 1.2: 20 °C 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / 0 - 20 °C / Inert atmosphere 3.1: hydrogenchloride / 1,4-dioxane / 20 °C 4.1: triethylamine / 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran / 20 °C / Sealed tube; Inert atmosphere
  • 26
  • [ CAS Unavailable ]
  • [ 114873-13-1 ]
  • [ 2819659-43-1 ]
YieldReaction ConditionsOperation in experiment
74% Stage #1: (R)-2-tert-butoxycarbonylamino-3-(3,4-dichlorophenyl)propionic acid With N-ethyl-N,N-diisopropylamine; HATU In 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran at 20℃; Inert atmosphere; Sealed tube; Stage #2: dimethyl amine In tetrahydrofuran; 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran at 20℃; 123.2 Step 2: tert-butyl N-[(lR)-1-[(3,4-dichlorophenyl)methyl]-2-(dimethylamino)-2-oxo- ethyl] carbamate In a sealed vialunder nitrogen, to a stirred solution of (2R)-2-(tert- butoxycarbonylamino)-3-(3,4-dichlorophenyl)propanoic acid (0.82 g, 2.47 mmol) and [dimethylamino(triazolo[4,5-b]pyridin-3-yloxy)methylene]-dimethyl- ammonium;hexafluorophosphate (98%, 1245 mg, 3.21 mmol) in DCM (11.217 mL) was added N-ethyl-N-isopropyl-propan-2-amine (0.65 mL, 3.70 mmol). The reaction was stirred at rt for 10 minutes then 2 M dimethylamine in THF (3.7 mL, 7.40 mmol) was added and the suspension was stirred overnight at rt. The resulting solution was diluted with DCM and an halfsaturated solutionof NaHCO3, and the aqueous layer was extracted twice with DCM. The organic layers were dried over phase separator, concentrated in vacuo and purified by flash chromatography on silica gel using a gradient of EtOAc in Heptane from 25% to 50% to afford the title compound as a colorless oil (661 mg, 74% yield, tr = 0.91 min). LCMS (Method F): m/z found 361.3 [M+H]+;1H-NMR (DMSO-d6, 400 MHz): δ (ppm) 7.61 - 7.49 (m, 2H), 7.26 (dd, J=8.3, 2.0 Hz, 1H), 7.08 (d, J=8.8 Hz, 1H), 4.56 (td, J=9.3, 5.1 Hz, 1H), 2.97 (s, 3H), 2.87 (dd, J=13.7, 5.0 Hz, 1H), 2.82 (s, 3H), 2.75 (dd, J=13.5, 9.7 Hz, 1H), 1.29 (s, 9H).
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