Diisopropylcarbodiimide → 2-((S)-2-tert-butoxycarbonylamino-3-phenyl-propionylamino)-thiazole-4-carboxylic acid methyl ester

HRID 2222949Notes

Reaction equation

HRID 2222949 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7]([NH2:10])[S:8][CH:9]=1)=[O:4].[C:11]([NH:18][C@H:19]([C:27](O)=[O:28])[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12].ON1C2C=CC=CC=2N=N1.C(N=C=NC(C)C)(C)C>ClCCl.CN(C)C=O>[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7]([NH:10][C:27](=[O:28])[C@@H:19]([NH:18][C:11]([O:13][C:14]([CH3:16])([CH3:15])[CH3:17])=[O:12])[CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[S:8][CH:9]=1)=[O:4]

Participants

7

Reactant 4

HCID 12734DiisopropylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 77857L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-HCID 840099Methyl 2-amino-1,3-thiazole-4-carboxylate

Product 1

HCID 866040392-((S)-2-tert-butoxycarbonylamino-3-phenyl-propionylamino)-thiazole-4-carboxylic acid methyl esterYield 81%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2-amino-thiazole-4-carboxylic acid methyl ester (2.4 g, 15.17 mmol), (S)—N-Boc-phenylalanine (4.518 g, 16.69 mmol), 1-hydroxybenzotriazole (2.255 g, 16.69 mmol) and 1,3-diisopropylcarbodiimide (2.127 g, 16.69 mmol) in a mixture of dichloromethane (50 mL) and N,N-dimethylformamide (25 mL) were stirred at ambient temperature for 24 hours. The mixture was diluted with dichloromethane, washed with water, brine and dried with magnesium sulfate. Evaporation of the solvents and chromatography of the residue over silica gel using a gradient between 0 and 25% ethyl acetate in dichloromethane gave 2-((S)-2-tert-butoxycarbonylamino-3-phenyl-propionylamino)-thiazole-4-carboxylic acid methyl ester (4.97 g, 81%).

Workup

  1. washwashed with water, brine
  2. dry with materialdried with magnesium sulfate
  3. customEvaporation of the solvents and chromatography of the residue over silica gel using a gradient between 0 and 25% ethyl acetate in dichloromethane

Sources & evidence

ORD record
ord-436f91dc43af401f872443f857346487
Source dataset
uspto-grants-2008_05
Patent number
US07371869B2

Reaction notes

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