L-Phenylalanine → Alanine, N-benzenesulfonyl-3-phenyl-, DL-

HRID 565584Notes

Reaction equation

HRID 565584 reaction equation
[C:1]1([S:7](Cl)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:11][C@H:12]([C:20]([OH:22])=[O:21])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>[OH-].[Na+]>[C:1]1([S:7]([NH:11][CH:12]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:20]([OH:22])=[O:21])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 6140L-PhenylalanineHCID 7369Benzenesulfonyl chloride

Product 1

HCID 38421Alanine, N-benzenesulfonyl-3-phenyl-, DL-

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent2×

Procedure

A mixture of 151 mmol (26.6 g) of benzenesulphonyl chloride and 50 ml of 4M aqueous sodium hydroxide is added to a solution of 37.8 mmol (6.25 g) of phenylalanine in 50 ml of 4M aqueous sodium hydroxide. The reaction mixture is stirred at room temperature for 24 hours. The solution is then rendered acidic to pH=2 with dilute hydrochloric acid and extracted with ether. The organic phase is dried over magnesium sulphate and concentrated. The resulting residue is recrystallised from ethanol to yield the expected compound.

Workup

  1. extractionrendered acidic to pH=2 with dilute hydrochloric acid and extracted with ether
  2. dry with materialThe organic phase is dried over magnesium sulphate
  3. concentrationconcentrated
  4. customThe resulting residue is recrystallised from ethanol

Sources & evidence

ORD record
ord-f1fa62cda032471091dfdcf3b195747a
Source dataset
uspto-grants-2001_01
Patent number
US06172108B2

Reaction notes

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