Water → HCID 9954958, compound

Participants

Reaction Steps

To a mixture of 0.302 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 30 ml of 1-hexanol is added 30 ml of water followed by 0.15 g of 10% palladium-on-carbon. The reaction mixture is then hydrogenated in a Parr apparatus at 54 psi for 23 hours. To the mixture is added 30 ml of water and the mixture is filtered through a pad of diatomaceous earth. The pad is washed with an additional 20 ml of water. The filtrate is transferred to a separatory funnel, the aqueous layer separated and the 1-hexanol layer is washed with 10 ml of water. The combined aqueous layers are washed with 100 ml of ethyl acetate and lyophilized to afford 0.144 g(82%) of the desired product. MS (ES), m/z:442.3 (M+H)+, 99.5% area percent pure by analytical HPLC.

Provenance & Evidence