L-Serine, methyl ester, hydrochloride (1:1) → HCID 90392794, compound

Participants

Reaction Steps

L-Serine methyl ester hydrochloride (5 g, 32.13 mmol) dissolved in methylene chloride (200 ml) was added with TEA (2 equiv., 8.95 ml) and in one portion 5-chlorothiophene-2-sulfonyl chloride (1.0 equiv., 6.97 g). The reaction was refluxed for 4 hours. The solvent was evaporated and the crude was dissolved in AcOEt (100 ml) and washed with water (1×80 ml) and brine. The organic phase was dried over sodium sulfate and concentrated under vacuum. The purification of the crude residue by crystallization from diethyl ether and petroleum ether afforded 10 g of the white product. Yield=93% 1HNMR (DMSO, 200 MHz) δ 2.81 (2H, q, J=7.2 Hz), 3.52 (3H, s), 3.92 (1H, t), 5.06 (1H, bs), 7.24 (1H, dd, J=4.2 Hz), 7.45 (1H, dd, J=4 Hz), 8.92 (1H, bs)

Provenance & Evidence