4-Methylmorpholine → 7-[2-(2-Tritylamino-4-thiazolyl)-acetamido]-3-acetylthiomethyl-ceph-3-eme-4-carboxylic acid

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Reaction Steps

A mixture of 9.9 g of 2-tritylamino-4-thiazolylacetic acid, 100 ml of tetrahydrofuran and 2.7 ml of N-methylmorpholine was stirred under an inert gas for 15 minutes at room temperature and was then cooled to -15° C after which 3.15 ml of isobutyl chloroformate were added. The mixture was stirred for 5 minutes at -10° to -15° C and then 6.5 g of the product of Step A, 65 ml of water and 3.15 ml of triethylamine were added over 2 minutes. The mixture was stirred for 11/2 hours at room temperature and the tetrahydrofuran was removed. The mixture was acidified and was extracted with methylene chloride. The mixture was vacuum filtered and the organic phase was washed and evaporated to dryness. The powdery residue was triturated with ether and dried to obtain 15.2 g of raw product. 6.7 g of of the said product were dissolved in methylene chloride and ethyl acetate was added thereto. The insoluble phase was removed and the solution was treated with carbon black and was vacuum filtered. The recovered product was rinsed and dried to obtain 5.1 g of 7-[2-(2-tritylamino-4-thiazolyl)-acetamido]-3-acetylthiomethyl-ceph-3-eme-4-carboxylic acid.

Provenance & Evidence