Hydrochloric Acid → HCID 10373871, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 7β-[(Z)-2-(2-t-butoxycarbonylaminothiazol-4-yl)-2-trityloxyiminoacetylamino]-3-(1,2,4-triazol-3-ylthiomethylthio)-3-cephem-4-carboxylic acid diphenylmethyl ester 1-oxide (2.71 g: 2.63 mMol.) in tetrahydrofuran (50 ml) at -78° C. is added a solution of lithium bis(trimethylsilyl)amide in tetrahydrofuran (1M: 2.9 ml), and the mixture is stirred at -78° C. for 10 minutes, mixed with trifluoromethanesulfonic acid methyl ester (0.33 ml: 2.92 mMol.), and stirred at -78° C. for 30 minutes. The reaction mixture is mixed with 10% hydrochloric acid (2.1 ml), diluted with water, and extracted with ethyl acetate. The extract is washed with aqueous sodium hydrogen carbonate and brine, dried over sodium sulfate, and concentrated. The residue is purified by silica gel chromatography (ethyl acetate) to give 7β-[(Z)-2-(2-t-butoxycarbonylaminothiazol-4-yl)-2-trityloxyiminoacetylamino]-3-(4-methyl-1,2,4-triazol-3-ylthiomethylthio)-3-cephem-4-carboxylic acid diphenylmethyl ester 1 -oxide (0.73 g) as pale brown foam. Yield: 27%. NMR δ(CDCl3 -CD3OD) ppm: 1.51(s, 9H), 3.31(s, 3H), 3.85(s, 2H), 4.12, 4.70(ABq, J=14.6 Hz, 2H), 4.74(d, J=4.8 Hz, 1H), 6.26(d, J=4.8 Hz, 1H), 6.96(s, 1H), 7.01(s, 1H), 7.2-7.5(m, 25H), 8.11(brs, 1H). IR ν(CHCl3) cm-1 : 3400, 1805, 1722, 1690, 1545, 1507, 1497, 1450, 1372, 1040.

Provenance & Evidence