L-Hydroxyproline → HCID 13136866, compound

Participants

Reaction Steps

A mixture of 5.20 g (30 mmol) of N-acetyl-3-hydroxy-L-proline and 75 ml of dichloromethane is cooled to -15° and 3.3 ml (30 mmol) of N-methyl morpholine and 2.33 ml (30 mmol) methyl chloroformate is added and stirring is continued for 20 minutes at -10° to -20°. A mixture of 3.06 g (15 mmol) of 6-amino-1,2-dihydro-2-oxo-3-quinolinecarboxylic acid, 120 ml of dichloromethane, 6.3 ml (45 mmol) of triethylamine, and 5.7 ml (45 mmol) of chlorotrimethylsilane is stirred at room temperature for 1/2 hour. The silylation mixture is cooled to -20 and the cold mixed anhydride of hydroxyproline is added and stirred for 4 hours with cooling and overnight at room temperature. The reaction mixture is evaporated to an oil which is treated with acetic acid and ethanol to yield 3.92 g of 6-[[(1-acetyl-4-hydroxy- 2-pyrrolidinyl)carbonyl]amino]-1,2-dihydro-2-oxo-3-quinolinecarboxylic acid.

Provenance & Evidence