Water → HCID 24820744, compound

Participants

Reaction Steps

To a solution of Boc-cyclopropylalanine p-nitrobenzyl Ester (4) (450 mg, 1.34 mmol) in MeOH (20 ml) was added 1N NaOH (2.6 ml, 2.6 mmol) at room temperature. After the mixture was stirred for 3 hr, water (10 ml) was added and the MeOH was removed in vacuo. The aqueous residue was washed with Et2O to remove p-nitrobenzyl alcohol and the aqueous layer was separated, cooled in an ice bath and 10% citric acid solution was added to pH 3. The mixture was saturated with NaCl and extracted with AcOEt and the extracts were washed with sat. NaCl solution, dried over Na2SO4 and evaporated in vacuo to give a white solid which was recrystallized from AcOEt-n-hexane to afford 260 mg of Boc-cyclopropyl Alanine (5) (96.3%) as colorless needles, mp 176°-177° C. (dec.); IR (KBr): 3230(NH), 1630-1680 (C=0). NMR (CDCl3 +DMSO)δ: 9.45 (br, s, IH, COOH), 5.88 (br, s, 1H, NH) 1.3-1.7 (m, 2H, CH2), 1.0-1.2 (m, 2H, CH2), 1.50 (s, 9H, Boc).

Provenance & Evidence