L-Phenylalanine → N-(N-Formyl-L-alpha-aspartyl)-3-phenyl-L-alanine

HRID 1252776Notes

Reaction equation

[OH-].[K+].[NH2:3][C@H:4]([C:12]([OH:14])=[O:13])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[CH:15]([NH:17][C@@H:18]1[C:23](=[O:24])[O:22][C:20](=[O:21])[CH2:19]1)=[O:16].[OH-].[Na+]>O>[CH:15]([NH:17][C@H:18]([C:23]([NH:3][C@H:4]([C:12]([OH:14])=[O:13])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:24])[CH2:19][C:20](=[O:21])[OH:22])=[O:16].[CH:15]([NH:17][C@H:18]([C:23]([OH:24])=[O:22])[CH2:19][C:20]([NH:3][C@H:4]([C:12]([OH:14])=[O:13])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:21])=[O:16]

Participants

Conditions

Temperature: -5 °C

Procedure

To an aqueous solution containing 13.2 g of potassium hydroxide dissolved in 330 ml of water was added 33.0 g (0.20 mole) of L-phenylalanine to form a solution. After being cooled to -5° C., the solution was fed little by little with 30.0 g (0.21 mole) of N-formyl-L-aspartic acid anhydride for one hour while maintaining its temperature at -5° C. to 5° C. A 10% aqueous sodium hydroxide solution was added thereto simultaneously to maintain the reaction liquid at a pH of 8-11. Thereafter, the reaction was carried out at the same temperature for one hour. The reaction mixture was analyzed by high speed liquid chromatography, with the result that the isomer formation ratio of N-formyl-α-L-aspartyl-L-phenylalanine to N-formyl-β- L-aspartyl-L-phenylalanine was 78:22 while the overall yield was 98% based on L-phenylalanine.

Workup

customto form a solution
customfor one hour
temperaturewhile maintaining its temperature at -5° C. to 5° C
temperaturesimultaneously to maintain
customthe reaction liquid at a pH of 8-11

Sources & evidence

ORD record: ord-9862de45861c4c85a49b2570d2a9ac68
Source dataset: uspto-grants-1988_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04745210

Reaction notes

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