1,2-Dichloroethane → HCID 57699995, compound

Participants

Reaction Steps

To a solution of (S)-2-tert-Butoxycarbonylamino-4-(tert-butyl-dimethyl-silanyloxy)-butyric acid (2.53 g, 7.6 mmol) in DCM (50 ml) at 0° C. was added cyclopentanol (1.39 ml, 15.3 ml), EDC (1.61 g, 8.4 mmol) and DMAP (0.093 g, 0.76 mmol). The reaction mixture was stirred for 16 hours at room temperature before evaporation under reduced pressure. The crude residue was dissolved in ethyl acetate (100 ml) and washed with 1M HCl, 1M Na2CO3 and brine. The organic layer was then dried over magnesium sulphate and evaporated under reduced pressure. The product was purified by column chromatography using ethyl acetate/heptane (1:4) to give 2.24 g, 73% yield of title compound. LCMS purity 100%, m/z 402.5 [M++H], 1H NMR (300 MHz, CDCl3), δ: 5.20 (1H, d, J=6.3 Hz), 5.15 (1H, m), 4.20 (1H, m), 3.6 (2H, m), 2.00 (1H, m), 1.95-1.55 (9H, bm), 1.40 (9H,s), 0.85 (9H,s), 0.10 (6H,s).

Provenance & Evidence