Sodium Bicarbonate → HCID 68820697, compound

Participants

Reaction Conditions

Reaction Steps

To a slurry of 2.0 g (13.77 mmol) of 4-amino-tetrahydro-furan-3-carboxylic acid methyl ester [WO 01/70673, Examples 46, 58] and 4-(2-methyl-quinolin-4-ylmethoxy)-benzenesulfonyl chloride hydrochloride (5.13 g, 15.15 mmol) in CH2Cl2 (20 mL) was added saturated aqueous NaHCO3 (20 mL) at 0° C. The solution was allowed to warm to 25° C. over 19 h. The reaction was then diluted with CH2Cl2 (100 mL) and water (30 mL). The organic layer was washed with water (2×50 mL)and then dried over MgSO4, filtered and concentrated to obtain a crude oil (5.13 g ). The crude product was purified by Biotage Flash 40M chromatography, eluting with 1:1 ethyl acetate-hexanes, to afford 4-[4-(2-methyl-quinolin-4-ylmethoxy)-benzenesulfonylamino]-tetrahydro-furan-3-carboxylic acid methyl ester as a white solid (2.3 g, 38%). MS: 457 (M+H)+

Provenance & Evidence