Hydrochloric Acid → HCID 86742710, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of 1.24 g (6.79 mmol) of 2-amino-N-(3,4-dihydroxyphenyl)acetamide in 30 ml of absolute acetonitrile was added 2.71 g (13.6 mmol) of N-methyl-N-(trimethylsilyl)trifluoroacetamide. After stirring for two hours, the clear solution was evaporated to dryness, finally at high vacuum at 55° C. The residue was dissolved in 30 ml of ethyl acetate (solution A). To a suspension of 1.5 g (6.79 mmol) of (S)-(2-oxo-3-azetidinyl)carbamic acid, phenylmethyl ester in 40 ml of ethyl acetate was added 0.96 g (6.79 mmol) of chlorosulfonyl isocyanate. After stirring for one hour, the solution was cooled to 0° C. and 15 ml of dichloromethane and subsequently 2.06 g (20.37 mmol) of triethylamine (dropwise) was added. To this mixture, solution A was added dropwise and after stirring overnight at room temperature, 30 ml of ice water was added. The pH was adjusted to 1 with 3N hydrochloric acid, the phases were separated and the organic phase was dried over sodium sulfate. After the evaporation of the solvent, the residue was triturated with ether, filtered and dried in vacuo; yield: 1.63 g.

Provenance & Evidence