Methanol → Methyl 2-[4-bromophenylsulfonyl]amino-3-phenylmethoxy-4-pentenoate

関与物質

反応手順

The 2-[[1,1-dimethylethoxy)carbonyl]amino-3-phenylmethoxy-4-pentenoic acid 63b (1.8 g, 5.37 mmol) is dissolved in methanol (54 mL) and thionyl chloride (8.3 mL) is added dropwise to the mixture. The resulting mixture is stirred at room temperature until the reaction is complete by tlc. The crude reaction is dried and re-evaporated from methanol (3 times). The dried reaction mixture is taken up in methylene chloride (30 mL) and triethylamine (7 mL). 4-Bromophenylsulfonyl chloride (1.23 g, 4.83 mmol) is added and the reaction is stirred overnight. The solvent is removed in vacuo and the oil is taken up in ethyl acetate, and then washed consecutively with 1N HCl, saturated sodium bicarbonate solution, and finally with brine, then dried over magnesium sulfate and the solvent removed in vacuo. The crude material is adsorbed onto silica gel and purified over a silica column eluting with hexane followed with hexane:ethyl acetate (8:2). Product fractions are combined and dried to give the desired product.

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