Trifluoroacetic acid → (S)-3-Amino-1-[[[[2-[[(3,4-dihydroxyphenyl)amino]carbonyl]hydrazino]sulfonyl]amino]carbonyl]-2-oxoazetidine

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Reaction Steps

At 0° C., 1.02 g (2.0 mmol) of (S)-[1-[[[[2-[[(3,4-dihydroxyphenyl)amino]carbonyl]hydrazino]sulfonyl]amino]carbonyl]-2-oxo-3-azetidinyl]carbamic acid, phenylmethyl ester was added to a mixture of 3.31 ml of trifluoroacetic acid and 0.78 ml (6.63 mmol) of thioanisole. After stirring overnight at room temperature, the dark brown solution was dropped into 40 ml of dry ether (0° C.) and the precipitated material was collected by suction (1.15 g) and stirred with 10 ml of dry dichloromethane; yield: 0.92 g. This material was used in the next step without further purification.

Provenance & Evidence