Sulfuric Acid → L-Aspartyl-L-phenylalanine

HRID 2073629Notes

Reaction equation

S(=O)(=O)(O)O.C([NH:8][C@H:9]([C:14]([NH:16][C@H:17]([C:25]([OH:27])=[O:26])[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:15])[CH2:10][C:11](=[O:13])[OH:12])=O>O>[NH2:8][C@H:9]([C:14]([NH:16][C@H:17]([C:25]([OH:27])=[O:26])[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:15])[CH2:10][C:11](=[O:12])[OH:13]

Participants

Conditions

Temperature: 50 °C

Procedure

A medium composed of 25.5 g of concentrated sulfuric acid and 72.5 g of water was heated to 50° C., followed by a gradual addition of 30.8 g (0.1 mole) of N-formyl-α-L-aspartyl-L-phenylalanine over about 1 hour. The reaction was conducted for further 3 hours at 50°-60° C. to remove the formyl group, so that α-L-aspartyl-L-phenylalanine was formed. The reaction mixture was then cooled to 20° C., and 9.6 g of methanol and 18.7 g of anhydrous magnesium chloride were added. The reaction mixture was heated to 30° C., followed by a reaction at 30°-35° C. for 4 days. As the reaction proceeded, crystals of α-APM hydrochloride precipitated little by little. After the reaction, the reaction mixture was cooled to 20° C., and the precipitated crystals were collected by filtration and washed with chilled water to obtain a wet α-APM.HCl cake containing 23.9 g of α-APM (as converted into its free form). Yield: 81.4% (based on N-formyl-α-L-aspartyl-L-phenylalanine).

Workup

customto remove the formyl group

Sources & evidence

ORD record: ord-943a5124166949d19b1915a31262fd08
Source dataset: uspto-grants-1990_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04918216

Reaction notes

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