Ethyl Acetate → HCID 68284162, compound

Participants

Reaction Steps

To a diastereoisomeric mixture of (1R,3S,5S) and (1S,3S,5R)-5-hydroxymethyl-2-aza-bicyclo[3.1.0]hexane-2,3-dicarboxylic acid 2-tert-butyl ester 3-ethyl ester (ratio 4:6, 100 mg, 0.31 mmol) in THF (1.5 mL) and H2O (0.15 mL) at 0° C. was added NaOH (1 M in water, 0.63 mL, 0.63 mmol). The solution was stirred 1 h at RT and poured into 10% KHSO4 (until pH 1), EtOAc was added and the layers were separated (×3). The combined organic layers were dried (Na2SO4), filtered and concentrated. The crude residue was used without further purification in the next step. MS (HPLC/MS): 256.2 [M−H]−, 258.3 [M+H]+, 280.3 [M+Na]+, 200.2 [MH−tBu]+, 515.54 [2M+H]+, 537.4 [2M+Na]+; tR (HPLC conditions f): 1.28 min.

Provenance & Evidence