Sodium Chloride → Methyl 2(S)-[N-(2-methylaminoethyl)-N-methylaminocarbonyloxy]-3-phenylpropionate

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Reaction Steps

To N,N'-dimethylethylenediamine (7.93 g) in N,N-dimethylformamide (27 ml) was dropwise added methyl 2(S)-phenoxycarbonyloxy-3-phenylpropionate (9.0 g) in N,N-dimethylformamide (9 ml) under cooling at -5°-10° C. over 30 minutes. After the dropwise addition, the mixture was stirred at said temperature for 60 minutes and poured into a mixture of ethyl acetate and 20% aqueous sodium chloride for partition. The water layer was re-extracted with ethyl acetate, the organic layer was combined, and 5% hydrochloric acid was added thereto for partition. The water layer was washed with ethyl acetate, added with methylene chloride, and adjusted to pH 9.0 with an aqueous solution of 24% sodium hydroxide. The organic layer was separated, washed with 20% aqueous sodium chloride, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure to give 8.64 g of methyl 2(S)-[N-(2-methylaminoethyl)-N-methylaminocarbonyloxy]-3-phenylpropionate (yield 97.9%).

Provenance & Evidence