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Chemical Structure| 27243-15-8 Chemical Structure| 27243-15-8

Structure of N-(Chloroacetoxy)succinimide
CAS No.: 27243-15-8

Chemical Structure| 27243-15-8

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Product Details of [ 27243-15-8 ]

CAS No. :27243-15-8
Formula : C6H6ClNO4
M.W : 191.57
SMILES Code : O=C(N1OC(CCl)=O)CCC1=O
MDL No. :MFCD11044492
InChI Key :OWZGNRBFMASABS-UHFFFAOYSA-N
Pubchem ID :12535337

Safety of [ 27243-15-8 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H302-H314
Precautionary Statements:P260-P264-P270-P280-P301+P330+P331-P303+P361+P353-P304+P340-P305+P351+P338-P310-P363-P405-P501
Class:8
UN#:3261
Packing Group:

Computational Chemistry of [ 27243-15-8 ] Show Less

Physicochemical Properties

Num. heavy atoms 12
Num. arom. heavy atoms 0
Fraction Csp3 0.5
Num. rotatable bonds 3
Num. H-bond acceptors 4.0
Num. H-bond donors 0.0
Molar Refractivity 42.13
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

63.68 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

1.16
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

-0.15
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

-0.55
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

0.5
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

0.46
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

0.28

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-0.74
Solubility 35.2 mg/ml ; 0.184 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Very soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-0.73
Solubility 35.4 mg/ml ; 0.185 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Very soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-0.82
Solubility 29.3 mg/ml ; 0.153 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble

Pharmacokinetics

GI absorption?

Gatrointestinal absorption: according to the white of the BOILED-Egg

High
BBB permeant?

BBB permeation: according to the yolk of the BOILED-Egg

No
P-gp substrate?

P-glycoprotein substrate: SVM model built on 1033 molecules (training set)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

No
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

No
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

No
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

No
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

No
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-7.58 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

0.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

1.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.55

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

2.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

No; 1 violation:MW<1.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

2.2

Application In Synthesis of [ 27243-15-8 ]

* 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 [ 27243-15-8 ]

[ 27243-15-8 ] Synthesis Path-Downstream   1~35

  • 1
  • [ 6066-82-6 ]
  • [ 79-04-9 ]
  • [ 27243-15-8 ]
YieldReaction ConditionsOperation in experiment
53% With triethylamine; In chloroform; at 0℃; for 0.416667h; To a solution of N-hydroxysuccinimide (640.3 mg, 5.56 mmol) in chloroform (8.5 mL) was added triethylamine (861.6 mu, 6.18 mmol) 0 C. Then, a-chloroacetyl chloride was added dropwise over a 5 minute period and stirred for an additional 20 minutes at 0C. The reaction mixture was washed with ice-cold water (15 mL) and brine (15 mL), concentrated to a volume of 1.7 mL in vacuo, then dried with sodium sulfate and filtered. To the resulting solution were added ethyl acetate (170 mu) and hexanes (1.2 mL), and the mixture was cooled down to 0 C stirred for 2 h, and a white solid was precipitated. It was filtered and washed first with ice-cold 10 mL portion of hexanes/ethyl acetate (4: 1), then with 10 mL hexanes/ethyl acetate (9: 1), and finally with hexanes (10 mL, twice). The resulting white solid was dried under house vacuum to yield 2,5-dioxopyrrolidin-l-yl 2-chloroacetate (563.9 mg, 53%). NMR 400 MHz (CDC13) delta 4.37 (s, 2H), 2.87 (s, 4H).
  • 2
  • [ 27243-15-8 ]
  • [ 142182-02-3 ]
  • [ 142182-09-0 ]
  • 3
  • [ 27243-15-8 ]
  • [ 79677-63-7 ]
  • 1-(N-benzyloxycarbonyl-3-iodo-L-tyrosyl)-2-chloroacetylhydrazine [ No CAS ]
  • 4
  • [ 27243-15-8 ]
  • 7-aminomethyl-1-azathioxanthone [ No CAS ]
  • 7-(N-methyl-2-chloro-acetamide)-1-azathioxanthone [ No CAS ]
  • 5
  • [ 27243-15-8 ]
  • [ 1004751-65-8 ]
  • [ 1004751-66-9 ]
  • 6
  • [ 27243-15-8 ]
  • bis(tricarbonyl(η-cyclopentadienyl)tungsten) [ No CAS ]
  • tricarbonylcyclopentadienyltungsten(II) chloride [ No CAS ]
  • (η(5)-cyclopentadienyl)[((succinimidooxy)carbonyl)methyl]tricarbonyltungsten [ No CAS ]
  • 7
  • [ 27243-15-8 ]
  • bis(tricarbonyl(η-cyclopentadienyl)tungsten) [ No CAS ]
  • (η(5)-cyclopentadienyl)[((succinimidooxy)carbonyl)methyl]tricarbonyltungsten [ No CAS ]
  • 8
  • [ 27243-15-8 ]
  • [ 16800-47-8 ]
  • tricarbonylcyclopentadienyltungsten(II) chloride [ No CAS ]
  • (η(5)-cyclopentadienyl)[((succinimidooxy)carbonyl)methyl]tricarbonyltungsten [ No CAS ]
  • 9
  • [ 27243-15-8 ]
  • cyclopentadienylmolybdenum tricarbonyl dimer [ No CAS ]
  • [ 159123-17-8 ]
  • 10
  • [ 27243-15-8 ]
  • [ 31202-69-4 ]
  • C13H23ClN2O5 [ No CAS ]
  • 11
  • 3-trifluoromethyl-4-amino-(methoxyethoxymethoxy)benzene [ No CAS ]
  • [ 27243-15-8 ]
  • 3-trifluoromethyl-4-(chloroethanoylamino)-(methoxyethoxymethoxy)benzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
52% In dichloromethane; at 20℃; 3-Trifluoromethyl-4- (2-chlorocarbamoylmethyl)methoxyethoxymethylbenzene; 3-Trifluoromethyl-4-amino-methoxyethoxymethylbenzene (0.5 g, 0.2 mmol), and N-hydroxysuccinimidyl chloroacetate(0.36 g, 0.2 mmol) were dissolved in dichloromethane (10 cm3), and stirred at room temperature overnight. Solvent was removed and the product purified using column chromatography on silica, (DCM/MeOH, Rf = 0.6, 5% MeOH/DCM) , followed by recrystallisation from hexane/EtOAc to give a white solid, (0.25 g, 52%), m.p. 72-740C, Found C, 45.76%,H, 4.63%, N, 4.21%. C13Hi5NO4F3Cl requires C, 45.72%, H,4.43%, N, 4.13%, m/z (ES+) :341 (M+), 364 [(M+Na)+], deltaH <n="42"/>(CDCl3, 400MHz) : 3.37(s, 3H, 0-CH3) , 3.55(t, J = 4.8 Hz, 2H,0-CH2), 3.81(t, J = 4.8Hz, 2H, O- CH2), 4.22 (s, 2H, CH2Cl),5.28 (s, 2H, 0-CH2-O)7 7.27 (d, J H-H«» = 8Hz, IH, Ar H ortho) , , 7.34 (s, IH, Ar H ortho) . 7.96 (d, JH-H(O) = 8Hz, IH, Ar H meta) , 8.57 (br s, IH, NH) . deltac (CDCl3, ' 100.6Hz) : 43.10(CH2C1), 59.25 (0-CH3), 68.09(0-CH2), 71.68 (0-CH2), 93.82(0-CH2-O), 114.65 (q, 2JCF = 18Hz, CCF3), 120.37(Ar CH),122.97 ( q, 1J0F = 162 Hz, CF3), 126.89 (Ar CH), 127.96 ( ArC), 154.82 (Ar C), 164.63 (Ar CH), 178.54 (C=O)], deltaF(CDCl3, 188MHz) : 61.5 (s) .
  • 12
  • [ 27243-15-8 ]
  • [ 1214248-39-1 ]
  • [ 1214248-45-9 ]
YieldReaction ConditionsOperation in experiment
100% In acetonitrile; at 23℃; for 1h; Step A: 2-Chloro-N-{2-[(R)-(1,2,3,4-tetrahydro-naphthalen-1-yl)amino]-4H-benzo[d][1,3]oxazin-6-yl}-acetamide A mixture of (R)-N2-(1,2,3,4-tetrahydro-naphthalen-1-yl)-4H-benzo[d][1,3]oxazine-2,6-diamine (Example 33) (293 mg, 1 mmol) and chloro-acetic acid 2,5-dioxo-pyrrolidin-1-yl ester (CAS 27243-15-8) (192 mg, 1 mmol) in acetonitrile (2 ml) was stirred at 23 C. for 1 h. Poured onto water and extracted with ethyl acetate, dried the combined organic layers over sodium sulfate, filtered off and evaporated totally to give the title compound as a light red oil (370 mg, 100%, HPLC 1.185 min), MS (ISP) m/e=370.1 [(M+H)+] and 372 [(M+2+H)+].
  • 13
  • [ 27243-15-8 ]
  • [ 56-41-7 ]
  • [ 691-80-5 ]
  • 14
  • [ 27243-15-8 ]
  • [ 61-90-5 ]
  • [ 688-12-0 ]
  • 15
  • [ 27243-15-8 ]
  • [ 73-32-5 ]
  • [ 67253-30-9 ]
  • 16
  • [ 27243-15-8 ]
  • C84H94N22O8 [ No CAS ]
  • C86H95ClN22O9 [ No CAS ]
  • 17
  • [ 27243-15-8 ]
  • [ 1235572-57-2 ]
  • [ 1235572-58-3 ]
  • 18
  • [ 27243-15-8 ]
  • [ 1042904-90-4 ]
  • [ 1316307-96-6 ]
  • 19
  • [ 27243-15-8 ]
  • (x)C2HF3O2*C41H72N24O10S3 [ No CAS ]
  • [ 76-05-1 ]
  • (x)C2HF3O2*C43H73ClN24O11S3 [ No CAS ]
  • 20
  • [ 27243-15-8 ]
  • C41H66N18O19S3 [ No CAS ]
  • C43H67ClN18O20S3 [ No CAS ]
  • 21
  • [ 27243-15-8 ]
  • C40H44N5O11PS2*C9H16N2 [ No CAS ]
  • [ 1421767-20-5 ]
YieldReaction ConditionsOperation in experiment
7% In acetonitrile; at 20℃; for 24h;pH 7.4; Compound 8 (30 mg, 29 ?mol) was dissolved in PBS-CH3CN (15 mL, 1:1, v/v). The mixture was added halo (I, Br, Cl) acetic acid NHS ester (12 mg, 42 ?mol in case of I) and stirred at rt for 6-24 h. The reaction mixture was diluted with EtOAc and washed with H2O. The organic solution was dried (Na2SO4), filtered and evaporated in vacuo. The residue was purified by column chromatography eluted with CHCl3-MeOH (10:1) to give 9 (17 mg, 63% : case of I).
  • 22
  • [ 27243-15-8 ]
  • [ 44604-32-2 ]
  • [ 1446684-71-4 ]
  • 23
  • [ 27243-15-8 ]
  • [ 1536470-97-9 ]
  • [ 1536470-98-0 ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; for 0.5h; To a solution of (2S)-2-propylpentyl 2-(((((((2R,3S,4R,5R)-5-(2-amino-6-oxo- 1H- purin-9(6H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(hydroxy)phosphoryl)oxy)(2- aminoethoxy)phosphoryl)amino)propanoate (15.0 mg, 0.019 mmol) in DMF (1 mL) were added DIPEA (16.7 mu, 0.096 mmol) and 2.17 (7.3 mg, 0.038 mmol) at ambient temperature. The reaction mixture was stirred at ambient temperature for 30 min. It was diluted with water (10 mL) and washed with dichloromethane (10 mL). The aqueous layer was concentrated in vacuo, diluted with water (1 mL), and directly purified by preparative reverse-phase HPLC (methanol/water gradient) to provide (2S)-2-propylpentyl 2-(((((((2R,3S,4R,5R)-5-(2-amino- 6-oxo-lH-purin-9(6H)-yl)-3,4-dihydroxytetrahydrofuran-2- yl)methoxy)(hydroxy)phosphoryl)oxy)(2-(2-chloroacetamido)ethoxy)phosphoryl)amino)- propanoate. MS m/z: 746.41 (M+l).
  • 24
  • [ 27243-15-8 ]
  • 2-(((((((2R,3S,4R,5R)-5-(2-amino-6-oxo-1H-purin-9(6H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(hydroxy)phosphoryl)oxy)(hydroxy)phosphoryl)oxy)ethylamine [ No CAS ]
  • [ 1536470-92-4 ]
YieldReaction ConditionsOperation in experiment
49% With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; for 1h; To a solution of 2-(((((((2R,3S,4R,5R)-5-(2-amino-6-oxo-lH-purin-9(6H)-yl)-3,4- dihydroxytetrahydrofuran-2- yl)methoxy)(hydroxy)phosphoryl)oxy)(hydroxy)phosphoryl)oxy)ethylamine (7.8 mg, 0.013 mmol) in DMF (1 mL) were added DIPEA (11.3 mu, 0.065 mmol) and 2,5-dioxopyrrolidin-l- yl 2-chloroacetate (5.0 mg, 0.026 mmol) at ambient temperature. The reaction mixture was stirred at ambient temperature for 1 h. It was diluted with water (10 mL) and washed with dichloromethane (10 mL). The aqueous layer was concentrated in vacuo, diluted with water (1 mL), and directly purified by preparative reverse-phase HPLC (methanol/water gradient) to provide (2-chloroacetamido)-(((((((2R,3S,4R,5R)-5-(2-amino-6-oxo-lH-purin-9(6H)-yl)- 3 ,4-dihydroxytetrahydrofuran-2- yl)methoxy)(hydroxy)phosphoryl)oxy)(hydroxy)phosphoryl)-oxy)ethane (4.3 mg, 49%). 1H 400 MHz NMR (D20) delta 8.47 (s, 1H), 8.01 (s, 1H), 5.94 (d, J = 6.6 Hz, 1H), 4.52 (del, J = 5.4, 3.0 Hz, 1H), 4.34-4.36 (m, 1H), 4.20-4.22 (m, 2H), 4.11 (s, 2H), 4.00-4.03 (m, 2H), 3.43-3.46 (m, 2H); MS m/z: 563.07 (M+l).
  • 25
  • [ 61-54-1 ]
  • [ 27243-15-8 ]
  • [ 52191-26-1 ]
  • 26
  • [ 27243-15-8 ]
  • [ 4499-07-4 ]
  • [ 80028-68-8 ]
  • 27
  • [ 27243-15-8 ]
  • 5'-d([5'-deoxy-5'-aminothymidine]CAC[5-(6-(1-(35-azido-3,6,9,12,15,18,21,24,27,30,33-undecaoxapentatriacontan-1-yl)-1H-triazole-4-yl)hexyne-1-yl)uridine]GCCCGC)-3' [ No CAS ]
  • 5'-d([(5'-deoxy-5'-chloroacetylamino)thymidine]CAC[5-(6-(1-(35-azido-3,6,9,12,15,18,21,24,27,30,33-undecaoxapentatriacontan-1-yl)-1H-triazole-4-yl)hexyne-1-yl)uridine]GCCCGC)-3' [ No CAS ]
  • 28
  • [ 27243-15-8 ]
  • 5'-d([5'-deoxy-5'-aminocytidine]CAG[5-(6-[1-(35-azido-3,6,9,12,15,18,21,24,27,30,33-undecaoxapentatriacontan-1-yl)-1H-1,2,3-triazol-4-yl]hex-1-yn-1-yl)cytidine]AGCGCA)-3' [ No CAS ]
  • 5'-d([(5'-deoxy-5'-chloroacetylamino)cytidine]CAG[5-(6-[1-(35-azido-3,6,9,12,15,18,21,24,27,30,33-undecaoxapentatriacontan-1-yl)-1H-1,2,3-triazol-4-yl]hex-1-yn-1-yl)cytidine]AGCGCA)-3' [ No CAS ]
  • 29
  • [ 27243-15-8 ]
  • 5'-d([5'-deoxy-5'-aminocytidine]CAT[5-(6-(1-(35-azido-3,6,9,12,15,18,21,24,27,30,33-undecaoxapentatriacontan-1-yl)-1H-triazole-4-yl)hexyne-1-yl)cytidine]GTCGGG)-3' [ No CAS ]
  • 5'-d([(5'-deoxy-5'-chloroacetylamino)cytidine]CAT[5-(6-(1-(35-azido-3,6,9,12,15,18,21,24,27,30,33-undecaoxapentatriacontan-1-yl)-1H-triazole-4-yl)hexyne-1-yl)cytidine]GTCGGG)-3' [ No CAS ]
  • 30
  • [ 27243-15-8 ]
  • [ 1613025-42-5 ]
  • [ 1613025-43-6 ]
YieldReaction ConditionsOperation in experiment
96% With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; for 1.5h; To a stirred solution of 22 (154 mg, 0.16 mmol) in dry DMF (3 mL) were added DIEA (83.2 muL, 0.48 mmol), and alpha-chloroacetylsuccinimidyl ester (36.5 mg, 0.19 mmol). The reaction mixture we stirred for 1.5 hrs at rt. After dilution with water, the reaction mixture was extracted with AcOEt (x2). The extracts were washed with sat. NaHCO3 aq. and brine followed by drying over Na2SO4. After removal of the solvent in vacuo, the residue was purified by column chromatography on SiO2 (chloroform : methanol = 30 : 1) to give 23 (159 mg, 96 %) as a yellow oil.
  • 31
  • [ 27243-15-8 ]
  • [ 1613025-46-9 ]
  • [ 1613025-47-0 ]
YieldReaction ConditionsOperation in experiment
94% With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; for 1.5h; Compound 26 (110 mg, 0.09 mmol) was used as a starting material. By the same synthetic procedure as that for 23, 27 (106 mg, 94%) was obtained as a colorless amorphous powder.
  • 32
  • [ 27243-15-8 ]
  • [ 1926-80-3 ]
  • N-chloroacetyl ω-aminocaproic acid methyl ester [ No CAS ]
  • 33
  • anhydrous methyl 3-aminoisovalerate hydrochloride [ No CAS ]
  • [ 27243-15-8 ]
  • N-chloroacetyl 3-amino-3-methylbutyric acid methyl ester [ No CAS ]
  • 34
  • [ 27243-15-8 ]
  • C38H46N8O5 [ No CAS ]
  • C40H47ClN8O6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
14 mg With triethylamine; In N,N-dimethyl-formamide; at 20℃; for 1h;Inert atmosphere; To a stirred solution of 2b (130 mg, 0.164 mmol) in CH2Cl2 (3.0 mL) was added TFA(2.0 mL) at room temperature. The mixture was allowed to stir for 1 h. The solvent wasco-evaporated twice with toluene (2 mL) to yield deprotected 2b (quantitative). To astirred solution of deprotected 2b (20 mg, 25 mumol) in dry DMF (2.0 mL) was addedEt3N (27.4 muL, 0.20 mmol) and <strong>[27243-15-8](2,5-dioxopyrrolidin-1-yl) 2-chloroacetate</strong> (7.0 mg, 37mumol) at room temperature. The mixture was allowed to stir for 1 h. After removing thesolvent in vacuo, the residue was purified by RP-HPLC (CH3CN (0.1% TFA) : H2O(0.1% TFA) = 10 : 90 (0 min) > 40 : 60 (30 min) > 100 : 0 (40 min) > 10 : 90 (45 min),detection: UV (220 nm)) to yield 2 (14 mg, 61%) as a yellow solid.
  • 35
  • [ 27243-15-8 ]
  • C45H59N9O8 [ No CAS ]
  • C47H60ClN9O9 [ No CAS ]
YieldReaction ConditionsOperation in experiment
6.2 mg With triethylamine; In N,N-dimethyl-formamide; at 20℃; for 2h;Inert atmosphere; To a stirred solution of 3c (130 mg, 0.164 mmol) in CH2Cl2 (3.0 mL) was added TFA(2.0 mL) at room temperature. The mixture was allowed to stir for 1 h. The solvent wasco-evaporated twice with toluene (2 mL) to yield deprotected 3c (quantitative). To astirred solution of deprotected 3c (14.7 mumol) in dry DMF (2.0 mL) was added Et3N(16.3 muL, 0.117 mmol) and <strong>[27243-15-8](2,5-dioxopyrrolidin-1-yl) 2-chloroacetate</strong> (5.2 mg, 27mumol) at room temperature. The mixture was allowed to stir for 2 h. After removing thesolvent in vacuo, the residue was purified by RP-HPLC (CH3CN (0.1% TFA) : H2O(0.1% TFA) = 10 : 90 (0 min) > 40 : 60 (30 min) > 100 : 0 (40 min) > 10 : 90 (45 min),detection: UV (220 nm)) to yield 3 (6.2 mg, 45%) as yellow oil.
 

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