Hydrochloric Acid → HCID 86755071, compound

Participants

Reaction Steps

To a solution of (3R,10S)-2-(aminomethyl)-5-methyl-3-(9-oxo-1,8-diaza-tricyclo [10.6.1.013,18 ]nonadeca-12 (19),13 (18),14,16-tetraen-10-ylcarbamoyl)hexanoic acid t-butyl ester (363 mg) and triethylamine (0.54 ml) in dry methylene chloride (20 ml) at 0° C. was added methanesulfonyl chloride (77 μml). The resulting mixture was stirred for 2 hours, allowing the mixture to rise to ambient temperature, then methylene chloride (100 ml) and 0.5N hydrochloric acid (50 ml) added, stirring vigorously. The aqueous layer was further extracted with methylene chloride (2×75 ml), then the combined organic layers washed with brine (100 ml). After drying the organic layer over MgSO4, it was filtered and evaporated to dryness. Purification of the residue by flash column chromatography (20-30% ethyl acetate/methylene chloride) gave (3R,10S)-2-(methylsulfonamidoaminomethyl)-5-methyl-3-(9-oxo-1,8-diaza-tricyclo[10.6.1.013,18 ]nonadeca-12(19),13(18),14,16-tetraen-10-ylcarbamoyl)hexanoic acid t-butyl ester as a white solid (211 mg).

Provenance & Evidence