Water → 2-Acetylthio-5-benzyloxycarbonylaminopentanoic acid

HRID 1447640Notes

Reaction equation

HRID 1447640 reaction equation
[S:1]1C=C[CH:3]=[C:2]1CC(O)=O.[C:10]([O:18][C:19]([NH:21][CH2:22][CH2:23][CH2:24][CH:25](Br)[C:26]([OH:28])=[O:27])=[O:20])(=O)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[OH2:30]>C(=O)([O-])[O-].[K+].[K+]>[C:2]([S:1][CH:25]([CH2:24][CH2:23][CH2:22][NH:21][C:19]([O:18][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:20])[C:26]([OH:28])=[O:27])(=[O:30])[CH3:3]

Participants

5

Reactant 3

HCID 962WaterHCID 159702-Thiopheneacetic acidHCID 203843135-Benzoyloxycarbonylamino-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-benzoyloxycarbonylamino-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-b7a5438640d94b2eab4365968d70b58d
Source dataset
uspto-grants-1979_12
Patent number
US04177277

Reaction notes

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