L-Phenylalanine → N-benzyloxycarbonyl-DL-3-phenylalanine

HRID 565581Notes

Reaction equation

HRID 565581 reaction equation
Cl[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].[NH2:12][C@H:13]([C:21]([OH:23])=[O:22])[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>[OH-].[Na+]>[CH2:5]([O:4][C:2]([NH:12][CH:13]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:21]([OH:23])=[O:22])=[O:3])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 6140L-PhenylalanineHCID 10387Benzyl chloroformate

Product 1

HCID 100081N-benzyloxycarbonyl-DL-3-phenylalanine

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent2×

Procedure

82 mmol (13.9 g) of benzyl chloroformate and 20 ml of 4M aqueous sodium hydroxide are added over a period of 30 minutes to a solution, cooled to 0° C., of 80 mmol (13.2 g) of phenylalanine in 20 ml of 4M aqueous sodium hydroxide. The solution returns to room temperature during a period of 1 hour. The reaction mixture is extracted with ether. The aqueous phase is rendered acidic to pH=2 with a dilute hydrochloric acid solution. The precipitate that forms is filtered off and washed to yield the expected compound.

Workup

  1. extractionThe reaction mixture is extracted with ether
  2. filtrationThe precipitate that forms is filtered off
  3. washwashed

Sources & evidence

ORD record
ord-810b89788abe4585bc4f0b7f9c8dd34c
Source dataset
uspto-grants-2001_01
Patent number
US06172108B2

Reaction notes

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