Beta-Propiolactone → HCID 54182937, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 3,4-dimethoxybenzenethiol (0.33 g, 1.9 mmol) in isopropanol (3 mL) is cooled in an ice-bath and 1 M sodium hydroxide (1.4 mL, 1.4 mmol) is added over 2 minutes. (3S,4S)-3-Methyl-4-(4-phenylbutyl)oxetan-2-one (0.28 g, 1.3 mmol) is dissolved in isopropanol (3 mL) and cooled to 0° C. Then the thiolate is added to the oxetanone solution over 3 minutes. This mixture is stirred with ice cooling for 5 minutes and then allowed to come to room temperature and stir 3 hours. The reaction is then acidified to pH 5 with HCl/ether. Methanol is added and the reaction mixture azeotroped several times until a semi-solid residue is obtained. The crude product is purified by column chromatography (silica, 1% MeOH in CH2Cl2) to give (2R,3R)-3-(3,4-dimethoxyphenylsulfanyl)-2-methyl-7-phenylheptanoic acid (0.35 g, 69%): 1H NMR (300 MHz, CDCl3) δ 7.28-7.23 (m, 2H), 7.19-7.11 (m, 3H), 7.04-6.97 (m, 2H), 6.76 (d, J=8.3 Hz, 1H), 3.84 (s, 3H), 3.83 (s, 3H), 3.27-3.25 (m, 1H), 2.72-2.68 (m, 1H), 2.56 (t, J=7.1 Hz, 2H), 1.63-1.47 (m, 6H), 1.26 (d, J=7.1 Hz, 3H); MS (EI) m/e 389 (M+H)+.

Provenance & Evidence