BOC-Ala-Gly-OBzl → (S)-2-(2-((tert-Butoxycarbonyl)amino)propanamido)acetic acid

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Reaction Steps

VII (16.97 g, 50 mmol) was taken in glacial acetic acid (170 ml) and hydrogenated overnight in the presence of 10% Pd/C (1.7 g) as catalyst at 40 psi. The catalyst was filtered with the aid of celite and solvent removed under reduced pressure. The residue was taken in satd. NaHCO3 solution, extracted with EtOAC (3×), cooled, acidified to pH 2.0 and re-extracted with EtOAC (3×). The combined EtOAC extracts were washed with Satd, NaCl, and concentrated under reduced pressure. The residue was triturated with EtOAC: Pet. ether(1:1) and the precipitate obtained was filtered, washed with pet. ether and dried (10.9 g, yield: 87.5%), Rf4 0.52. Anal Calcd. for C10H18N2O5 ·1/2H2O: C 46.50, H 7.41, N 10.84%. Found: C 46.64, H 7.41, N 10.84%.

Provenance & Evidence