Sodium hydride → HCID 53686285, compound

HRID 233369Notes

Reaction equation

HRID 233369 reaction equation
Br[C@H:2]([CH:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH2:7][CH3:8])[C:3]([OH:5])=[O:4].[C:15]([OH:18])(=[S:17])[CH3:16].[H-].[Na+]>CN(C)C=O>[C:15]([S:17][C@@H:2]([CH:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH2:7][CH3:8])[C:3]([OH:5])=[O:4])(=[O:18])[CH3:16]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 54347224HCID 54347224, compoundHCID 178418634HCID 178418634, compound

Product 1

HCID 53686285HCID 53686285, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of (R)-2-bromo-3-phenylpentanoic acid in dimethylformamide is added to a solution of thioacetic acid (1.5 equivalents) and sodium hydride (2.5 equivalents) in anhydrous dimethylformamide. The mixture is stirred for 3 hours at a temperature close to 20° C. After customary treatment, (S)-2-acetylthio-3-phenylpentanoic acid is obtained with a yield of 78% in the form of a yellow oil having the following characteristics: Rf =0.44 [methylene chloride/methanol (9:1 by volume)].

Workup

  1. customclose to 20° C

Sources & evidence

ORD record
ord-0d855c62af254a12ab3040815243ab60
Source dataset
uspto-grants-1997_01
Patent number
US05591891

Reaction notes

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