Hydrochloric Acid → HCID 67102919, compound

Participants

Reaction Conditions

Reaction Steps

A 25 mL round-bottomed flask was charged with (3R,5S)-5-(((1R,2S)-1-(cyclopropylsulfonylcarbamoyl)-2-vinylcyclopropyl)carbamoyl)pyrrolidin-3-yl 4-chloroisoindoline-2-carboxylate hydrochloride (0.500 g, 0.894 mmol), (S)-2-(tert-butoxycarbonyl)-2-cyclohexylacetic acid (276 mg, 1.07 mmol) and HATU (408 mg, 1.07 mmol) in dry DMF (9 mL). The solution was cooled on an ice-water bath and treated with DIEA (0.467 mL, 2.68 mmol) by dropwise addition. The mixture was stirred at 0° C. for 1 h, then allowed to warm up and stirred at room temperature for 16 h. The mixture was diluted with water (50 mL) and the pH adjusted to 3 with 1N HCl, the mixture was extracted with Et2O (3×20 mL). The combined organic extracts were then washed with 1N HCl (3×20 mL), water (3×20 mL) and brine (3×20 mL). The organic extract was then dried over MgSO4, filtered and concentrated. The crude material was the purified by chromatography (Biotage) eluting with 1-3% MeOH—CH2Cl2 to give the product as a white foam, (394 mg, 59%). MS m/e 662 (M+−Boc).

Provenance & Evidence