Water → HCID 9954958, compound

Participants

Reaction Steps

To a mixture of 1.0 g 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 in 50 ml of 1-pentanol is added 50 ml of water followed by 0.5 g of 10% palladium-on-carbon. The reaction mixture is then hydrogenated in a Parr apparatus at 54 psi for 20 hours. The mixture is filtered through a pad of diatomaceous earth and the pad washed with an additional 40 ml of water. The filtrate is transferred to a separatory funnel, and the aqueous layer separated. The 1-pentanol layer is washed with an additional 10 ml of water. The combined aqueous layers are washed with 100 ml of ethyl acetate and lyophilized to afford 0.47 g(81%) of the desired product. MS (ES), m/z:442.3 (M+H)+, 98% area percent pure by analytical HPLC.

Provenance & Evidence