Water → 2-Acetylthio-5-benzyloxycarbonylaminopentanoic acid

HRID 614798Notes

Reaction equation

HRID 614798 reaction equation
[S:1]1C=C[CH:3]=[C:2]1CC(O)=O.[CH2:10]([O:17][C:18]([NH:20][CH2:21][CH2:22][CH2:23][CH:24](Br)[C:25]([OH:27])=[O:26])=[O:19])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[OH2:29]>C(=O)([O-])[O-].[K+].[K+]>[C:2]([S:1][CH:24]([CH2:23][CH2:22][CH2:21][NH:20][C:18]([O:17][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:19])[C:25]([OH:27])=[O:26])(=[O:29])[CH3:3]

Participants

5

Reactant 3

HCID 962WaterHCID 159702-Thiopheneacetic acidHCID 203843115-{[(Benzyloxy)carbonyl]amino}-2-bromopentanoic acid

Product 1

HCID 203843142-Acetylthio-5-benzyloxycarbonylaminopentanoic acid

Reagents, catalysts & solvents 1

HCID 11430Potassium CarbonateSolvent

Procedure

Thiolacetic acid (1 g.) is added to a solution of 5-benzyloxycarbonylamino-2-bromopentanoic acid [Chem. Pharm. Bull., 24, 326 (1976)] (3.3 g.) in a mixture of water (30 ml.) and potassium carbonate (1.38 g.). The mixture is stirred at room temperature overnight, acidified and extracted with ethyl acetate to yield 2-acetylthio-5-benzyloxycarbonylaminopentanoic acid.

Workup

  1. extractionextracted with ethyl acetate

Sources & evidence

ORD record
ord-7c2d4e135e5a49a19003ed4940e607b5
Source dataset
uspto-grants-1979_03
Patent number
US04146611

Reaction notes

Loading…