L-Alanine → (S)-2-(phenylsulfonamido)propanoic acid

HRID 2290957Notes

Reaction equation

HRID 2290957 reaction equation
[NH2:1][C@H:2]([C:4]([OH:6])=[O:5])[CH3:3].[C:7]1([S:13](Cl)(=[O:15])=[O:14])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>[OH-].[Na+]>[C:7]1([S:13]([NH:1][C@H:2]([C:4]([OH:6])=[O:5])[CH3:3])(=[O:15])=[O:14])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 5950L-AlanineHCID 7369Benzenesulfonyl chloride

Product 1

HCID 7114743(S)-2-(phenylsulfonamido)propanoic acidYield 95%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

N-benzenesulfonylalanine was prepared by mixing equimolar quantities of alanine and benzenesulfonyl chloride at 60° C. in aqueous sodium hydroxide (200 mol%). A 95% yield was obtained. The method is set out in the previously mentioned book "Chemistry Of The Amino Acids".

Workup

  1. customA 95% yield was obtained

Sources & evidence

ORD record
ord-426399edc266420e8327c4a0943796f2
Source dataset
uspto-grants-1986_10
Patent number
US04618710

Reaction notes

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