Sodium Iodide → HCID 53848558, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of trityl-3-chloromethylthio-1,2,4-triazole (11.5 g: 30.0 mMol.) in acetone (150 ml) is added sodium iodide (9.00 g: 60.0 mMol.), and the mixture is stirred t 50° C. for 3 hours. The reaction mixture is diluted with water and extracted with ethyl acetate. The extract is washed with brine, dried over sodiumsulfate, and concentrated to give trityl-3-iodomethylthio-1,2,4-triazole as yellow crystals [NMR δ (CDCl3) ppm: 4.70(s, 2H), 7.1 to 7.2(m, 6H), 7.3 to 7.4(m, 9H), 7.96(s, 1H) : 13 g]. To a solution of 7β-[(Z)-2-(2-t-butoxycarbonylaminothiazol-4-yl) -2-trityloxyiminoacetylamino-3-argentiothio-3-cephem- 4-carboxylic acid diphenylmethyl ester 1-oxide (16.8 g : 15 mMol.) in hexamethylphosphoramide (90 ml) is added trityl-3-iodomethylthio -1,2,4-triazole (13 g). and the mixture is stirred at room temperature for 3 hours. The reaction mixture is diluted with ethyl acetate mixed with saturated brine, and filtered through Celite. The organic layer is taken, washed with brine, dried over sodium sulfate, and concentrated. The residue is purified by silica gel chromatography (toluene : ethyl acetate=5:1-3:1) to give 7β-[(Z)-2-(2-t-butoxycarbonylaminothiazol-4-yl)-2-trityloxyiminoacetylamino]-3-(trityl-1,2,4-triazol-3-ylthiomethylthio) -3-cephem-4-carboxylic acid diphenylmethyl ester 1- oxide (11.29 g) as Pale brown foam. Yield: 59%. NMR δ (CDCl3) ppm: 1.49(s, 9H), 3.19, 3.82(ABq, J=18.5Hz, 2H), 4.19(d, J=4.6Hz, 1H), 4.16, 4.22(ABq, J=13.7Hz, 2H), 6.19(dd, J=4.6Hz, J=10.1Hz, 1H), 6.97(s, 1H), 7.05-7.5(m, 41H), 7.90(s, 1H), 8.04(d, J=10.1Hz, 1H), 8.30(brs, 1H). IR ν (CHCl3) cm-1 : 3400, 1804, 1725, 1689, 1543, 1496, 1449, 1371, 1040. 2) Acyl=(Z)-2-(2-t-butoxycarbonylaminothiazol-4-yl)-2-trityloxyiminoacetyl: Het=1-methyl-1.2.4-triazol-3-yl (4E3-2)

Provenance & Evidence