Sodium Sulfate → HCID 11539062, compound

Participants

Reaction Steps

A mixture of 6,8-difluoro-3,4-dihydro-1H-naphthalen-2-one (182 mg, 1.0 mmol), 2-amino-pentanoic acid (5-tert-butyl-[1,3,4]thiadiazol-2-yl)-amide HCl (293 mg, 1.0 mmol) in methylene chloride (25 mL) was treated with triethyl amine (0.14 mL), then acetic acid (0.27 mL) and sodium sulfate. After stirring for 15 min, 95% pure sodium triacetoxy borohydride (424 mg, 2.0 mmol) was added and the resulting mixture was stirred at rt overnight. The mixture was quenched with dilute water and extracted with methylene chloride. The organic layer was washed with dilute sodium bicarbonate to pH 8, separated, dried and concentrated to give 322 mg of the title compound as a yellow glass foam, LC-MS, RT=2.2 min, M+1=423.0. The glass foam was purified by HPLC to give the trifluoroacetic acid salt of the title compound as a brown solid, LC-MS, RT=2.3 min, M+1=423.0.

Provenance & Evidence