Toluene → HCID 57255092, compound

Participants

Reaction Conditions

Reaction Steps

Trifluoroacetic acid (4.7 ml) was added dropwise to a stirred suspension of (3S)-2-[[1(2-amino-4-thiazolyl)-2-[[1-[[[[[(1,4-dihydro-5-hydroxy-4-oxo-2-pyridinyl)methyl]amino]sulfonyl]amino]carbonyl]-2-oxo-3-azetidinyl]amino]-2-oxoethylidene]amino]oxy]-2-methylpropanoic acid, diphenylmethyl ester (131 mg, 0.113 mmole) in 3 ml of dichloromethane and 0.3 ml anisole at 0° C. After stirring 45 minutes at 5° C., 2 ml of toluene was added and the volatiles were removed in vacuo. The resulting oil was washed with hexane (3×4 ml) and triturated to a solid with 10 ml of ether. The solid was washed once with ether (10 ml) and dried in vacuo. The above reaction and work-up were repeated on 0.166 mmole of (3S)-2-[[[1-(2-amino-4-thiazolyl)-2-[[1-[[[[[(1,4-dihydro-5-hydroxy-4-oxo-2-pyridinyl)methyl]amino]sulfonyl]amino]carbonyl] -2-oxo-3-azetidinyl]amino]-2-oxoethylidene]amino]oxy]-2-methylpropanoic acid, diphenylmethyl ester. The crude solids were combined, dissolved in 2 ml of acetonitrile-water (40-60) (pH 2.5) and chromatographed on a column (200 ml) of macroreticular styrene-divinylbenzene copolymer, using an acetonitrile-water gradient. The desired material eluted at acetonitrile-water (20-80). The relevant fractions were combined and lyophilized to afford 103 mg of the title compound as a white solid, melting point 180° C., dec.

Provenance & Evidence