2-Benzyloxycarbonylamino-3-(1-methylcyclopentyl)propionic acid methyl ester → HCID 67392027, compound

Participants

Reaction Steps

2-Benzyloxycarbonylamino-3-(1-methylcyclopentyl)-propionic acid methyl ester (7.6 g, 23.8 mmol) was dissolved in a mixture of acetonitrile (82 mL) and 0.2 M aqueous NaHCO3 (158 mL) and Alcalase 2.4 L (1.1 mL) was added and the reaction mixture wa stirred vigorously for 8 h. The reaction mixture was then evaporated at 30° C. to remove acetonitrile, and the aqueous residue was washed with ether. The ethereal layer was concentrated to yield 1.9 g of (R)-2-benzyloxycarbonylamino-3-(1-methylcyclopentyl)-propionic acid methyl ester. The aqueous phase was filtered with Celite, the pH was adjusted to 3 with 6 N HCl, and the solution was extracted with ethylacetate. The ethyl acetate layer was dried and evaporated to yield 1.4 g of (S)-2-benzyloxycarbonylamino-3-(1-methyl-cyclopentyl)-propionic acid. MS: 304.2 (M−1), 306.0 (M+1), 327.9 (M+Na).

Provenance & Evidence