Cyanuric chloride → HCID 42628061, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 44 mg cyanuric chloride in 1.5 ml 1,2-dimethoxyethane were added 0.03 ml N-methylmorpholine. The resulting white suspension was treated with 150 mg (2S,4R)-4-[(5-chloro-thiophene-2-carbonyl)-amino]-1-{[2-fluoro-4-(2-oxo-pyridin-1-yl)-phenylcarbamoyl]-methyl}-pyrrolidine-2-carboxylic acid (example 12) in 0.5 ml 1,2-dimethoxyethane and stirred at r.t for 3 hrs. The precipitate was filtered off. The filtrate was cooled to 0° C. A solution of 13 mg NaBH4 in 0.7 ml H2O was added dropwise. The mixture was stirred for 5 min at 0° C., then diluted with water and extracted with EtOAc. The organic layer was washed with water, dried over MgSO4, filtrated and concentrated. The crude product was purified by chromatography (silica gel; gradient: CH2Cl2->CH2Cl2/MeOH 9:1) to give 20 mg 5-chloro-thiophene-2-carboxylic acid ((3R,5S)-1-{[2-fluoro-4-(2-oxo-pyridin-1-yl)-phenylcarbamoyl]-methyl}-5-hydroxymethyl-pyrrolidin-3-yl)-amide. White solid. MS 505.4 ([M+H]+)

Provenance & Evidence