1-Butanol → HCID 9954958, compound

Participants

Reaction Steps

A mixture of 4-nitrobenzyl (4R,5S,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-3-{[(2R,3R)-2-({[(2S)-3-methyl-2-({[(4-nitrobenzyl)oxy]carbonyl}amino)-butanoyl]amino}methyl)tetrahydrofuran-3-yl]thio}-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (0.200 g), 50% wet 10% palladium on carbon (0.256 g), 1-butanol (20 ml) and water (20 ml) is hydrogenated in a Parr apparatus at 56 psi for 8 hours. The catalyst is then removed by filtration through diatomaceous earth and washed with 2×6 ml of water. The 1-butanol layer is extracted once with 6 ml of water. The combined aqueous solution (ca. 38 ml) is extracted twice with 2×10 ml of isopropyl acetate, concentrated under reduced pressure below 28° C. to ca. 20 ml and lyophilized to give 97.1 mg (83.0%) of the desired product as a slightly tan solid. MS (ES), m/z:442.3 (M+H)+; rotation [α]D25+42±1° (c 0.84, H2O); purity by analytical HPLC (100%).

Provenance & Evidence