Hydrochloric Acid → HCID 178467028, compound

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Reaction Steps

The (RS)-(3,5-diethoxy-2-fluoro-phenyl)-[4-(N-hydroxycarbamimidoyl)-phenylamino]-acetic acid ethyl ester (44 mg) described in example 2.5 was dissolved in THF (0.5 ml). IM NaOH (0.21 ml) was added and the mixture was stirred for 2 h at room temperature. The mixture was neutralized with 1 M HCl, concentrated and purified by column chromatography to give 23 mg of (RS)-(3,5-diethoxy-2-fluoro-phenyl)-[4-(N-hydroxycarbamimidoyl)-phenylamino]-acetic acid as a colorless solid. MS: 392 ([M+H]+) This compound was separated into the enantiomers by preparative HPLC on a chiral stationary phase (Chiralpak AD) using heptane/isopropanol/trifluoroacetic acid (60:40:0.2) as a mobile phase to give, after neutralisation, (R)-(3,5-diethoxy-2-fluoro-phenyl)-[4-(N-hydroxycarbamimidoyl)-phenylamino]-acetic acid and (S)-(3,5-diethoxy-2-fluoro-phenyl)-[4-(N-hydroxycarbamimidoyl)-phenylamino]-acetic acid.

Provenance & Evidence