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

HRID 64784

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]([NH:23][C@H:24]([C:29]([OH:31])=[O:30])[CH2:25][C:26]([OH:28])=[O:27])([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14].S(=O)(=O)(O)O>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]([NH:23][C@H:24]([C:29]([OH:31])=[O:30])[CH2:25][C:26]([OH:28])=[O:27])([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14]

Participants

Conditions

Temperature: 60 °C

Procedure

Eight grams of DL-phenylalanine, 8.1 g of N-carbobenzoxy-L-aspartic acid and 1.2 g of sulfuric acid were added to 100 ml of water and the resulting solution was heated to 60° C. This solution was cooled to 40° C. at a rate of 2° C. per hour while stirring, and was stirred for another two hours. The resulting crystal was separated, washed in 20 ml of water and dried to give 8.2 g of an L-phenylalanine/N-carbobenzoxy-L-aspartic acid salt. Analysis of this salt revealed that the optical purity of the L-phenylalanine was 97%.

Workup

temperatureThis solution was cooled to 40° C. at a rate of 2° C. per hour
stirringwas stirred for another two hours
customThe resulting crystal was separated
washwashed in 20 ml of water
customdried

Sources & evidence

ORD record: ord-1152c779a032460a9d26c9a5a8e4f462
Source dataset: uspto-grants-1986_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04610827

Linked notes

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