Ethyl Acetate → N-[(1,1-Dimethylethoxy)carbonyl]-L-homoserine cyclopentyl ester

Participants

Reaction Conditions

Reaction Steps

(S)-2-tert-Butoxycarbonylamino-4-(tert-butyl-dimethyl-silanyloxy)-butyric acid cyclopentyl ester (1.57 g, 3.9 mmol) was dissolved in acetic acid:THF:water (3:1:1, 100 ml). The reaction mixture was stirred at 30° C. for 16 hours for complete reaction. Ethyl acetate (200 ml) was added and washed with 1M Na2CO3, 1M HCl and brine. The ethyl acetate extracts were dried over magnesium sulphate and evaporated under reduced pressure to give the product as a clear oil which crystallised on standing (1.0 g, 95%). LCMS purity 100%, m/z 310.3 [M++Na], 1H NMR (300 MHz, CDCl3), δ: 5.40 (1 H, d, J=6.5 Hz), 5.20 (1 H, m), 4.40 (1H, m), 3.65 (2H, m), 2.15 (1H, m), 1.90-1.55 (9H, bm), 1.45 (9H, s).

Provenance & Evidence