Sodium Hydroxide → HCID 59616761, compound

Participants

Reaction Steps

(3S)-ethyl 2-azabicyclo[2.2.1]heptane-3-carboxylate (1.25 g, 7.39 mmol), (S)-2-(methoxycarbonylamino)-3-methylbutanoic acid (1.42 g, 8.13 mmol), diisopropylethylamine (6.45 mL, 36.9 mmol), and HATU (2.95 g, 7.76 mmol) were combined in dimethylformamide (40 mL) at ambient temperature and stirred for 2 hours. The solution was diluted with water and the product filtered and dried. The dried ester (1.0 g, 3.06 mmol) was taken up in water (15 mL) and ethanol (15 mL) and treated with sodium hydroxide (0.5 g, 12.5 mmol) at ambient temperature for 17 hours. The solution was washed with ether then the aqueous was neutralized with concentrated HCl to pH 7 and the product extracted into ethyl acetate, dried over sodium sulfate, and concentrated to give the title compound as a waxy solid.

Provenance & Evidence