Diethyl Ether → 2-(2-Amino-1,3-thiazol-4-yl)-2-[3-(3,4-diacetoxybenzoyl)carbazoyl]methoxyiminoacetic acid tert-butyl ester hydrochloride

Participants

Reaction Steps

In 50 ml of methylene chloride was suspended 6.12 g (19.4 mmole) of 2-(2-amino-1,3-thiazol-4-yl)-2-carbazoylmethoxyiminoacetic acid tert-butyl ester, and to the suspension was added 20.8 g (102.3 mmole) of N,O-bis(trimethylsilyl)acetamide to form a solution. To the ice-cooled solution was added 5.467 g (21.3 mmole) of 3,4-diacetoxybenzoic acid chloride and the mixture was stirred for 2 hours under ice-cooling. The resulting mixture was poured into 800 ml of ether and to the mixture was added a small amount of methanol while stirring. Resulting precipitates were collected by filtration, washed with ether and then dried to obtain 10.2 g of 2-(2-amino-1,3-thiazol-4-yl)-2-[3-(3,4-diacetoxybenzoyl)carbazoyl]methoxyiminoacetic acid tert-butyl ester hydrochloride. (Yield: 98.2%)

Provenance & Evidence