Dl-Phenylalanine → L-phenylalanine N-benzenesulfonyl-L-aspartic acid

HRID 64786

Reaction equation

HRID 64786 reaction equation
[NH2:1][CH:2]([C:10]([OH:12])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:13]1([S:19]([NH:22][C@H:23]([C:28]([OH:30])=[O:29])[CH2:24][C:25]([OH:27])=[O:26])(=[O:21])=[O:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.S(=O)(=O)(O)O.[OH-].[Na+]>O>[NH2:1][C@H:2]([C:10]([OH:12])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:13]1([S:19]([NH:22][C@H:23]([C:28]([OH:30])=[O:29])[CH2:24][C:25]([OH:27])=[O:26])(=[O:20])=[O:21])[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 994Dl-PhenylalanineHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 10989413N-benzenesulfonyl-L-aspartic acid

Product 1

HCID 86740983L-phenylalanine N-benzenesulfonyl-L-aspartic acidYield 35.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

Six grams of DL-phenylalanine, 5.4 g of N-benzenesulfonyl-L-aspartic acid and 1.8 g of sulfuric acid were dissolved in 110 ml of water. While this solution was continuously stirred at 50° C., a 10% aqueous solution of caustic soda (7.3 ml) was added over five hours. The resulting crystal was separated, washed with 10 ml of water and dried to give 3.1 g of an L-phenylalanine/N-benzenesulfonyl-L-aspartic acid salt. Analysis of this salt revealed that the optical purity of the L-phenylalanine was 94%.

Workup

  1. customThe resulting crystal was separated
  2. washwashed with 10 ml of water
  3. customdried

Sources & evidence

ORD record
ord-c087e91160fd4e2da6eb826b5be34b36
Source dataset
uspto-grants-1986_09
Patent number
US04610827

Linked notes

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