Dl-Phenylalanine → D-phenylalanine N-carbobenzoxy-D-aspartic acid

HRID 64785

Reaction equation

HRID 64785 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.S(=O)(=O)(O)O.[C:18]([NH:28][C@@H:29]([C:34]([OH:36])=[O:35])[CH2:30][C:31]([OH:33])=[O:32])([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19]>O>[C:18]([NH:28][C@@H:29]([C:34]([OH:36])=[O:35])[CH2:30][C:31]([OH:33])=[O:32])([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19].[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

Participants

5

Reactant 3

HCID 994Dl-PhenylalanineHCID 1118Sulfuric AcidHCID 5289152(2R)-2-(((benzyloxy)carbonyl)amino)butanedioic acid

Product 1

HCID 13714281D-phenylalanine N-carbobenzoxy-D-aspartic acidYield 32.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Eight grams of DL-phenylalanine and 1.2 g of sulfuric acid was suspended in 100 ml of water at 40° C. Ten grams of N-carbobenzoxy-D-aspartic acid was added to the solution over five hours, while this solution was continuously stirred. The resulting crystal was separated, washed with 10 ml of water and dried to give 5.2 g of a D-phenylalanine N-carbobenzoxy-D-aspartic acid. Analysis revealed that the optical purity of the D-phenylalnine was 98%.

Workup

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

Sources & evidence

ORD record
ord-987bea95ecff469face1ae081f9f5f8e
Source dataset
uspto-grants-1986_09
Patent number
US04610827

Linked notes

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