2,2,2-Trichloroethyl chloroformate → HCID 70002349, compound

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Reaction Steps

In analogy to example 1.10, the (RS)-(4-carbamimidoyl-phenylamino)-[5-ethoxy-2-fluoro-4-(2-hydroxy-ethoxy)-phenyl]-acetic acid ethyl ester hydrochloride described in example 1.6 was converted to (RS)-{4-[amino-(2,2,2-trichloro-ethoxycarbonylimino)-methyl]-phenylamino}-[5-ethoxy-2-fluoro-4-(2-hydroxy-ethoxy)-phenyl]-acetic acid ethyl ester by a reaction with 2,2,2-trichloroethyl chloroformate. MS: 596 ([M+H]+) This compound was separated into the enantiomers by preparative HPLC on a chiral stationary phase (Chiralpak AD) using heptane/ethanol/diethylamine (60:40:0.2) as a mobile phase to give (S)-{4-[amino-(2,2,2-trichloro-ethoxycarbonylimino)-methyl]-phenylamino}-[5-ethoxy-2-fluoro-4-(2-hydroxy-ethoxy)-phenyl]-acetic acid ethyl ester and (R)-{4-[amino-(2,2,2-trichloro-ethoxycarbonylimino)-methyl]-phenylamino}-[5-ethoxy-2-fluoro-4-(2-hydroxy-ethoxy)-phenyl]-acetic acid ethyl ester. As a by-product, there was obtained (RS)-{4-[amino-(2,2,2-trichloro-ethoxycarbonylimino)-methyl]-phenylamino}-{5-ethoxy-2-fluoro-4-[2-(2,2,2-trichloro-ethoxycarbonyloxy)-ethoxy]-phenyl}-acetic acid ethyl ester. MS: 770.

Provenance & Evidence