Sodium Hydroxide → HCID 67229365, compound

Participants

Reaction Conditions

Reaction Steps

A 0° C. solution of tert-butyl (1S,4S)-5-{[(1S,3R)-3-amino-1-ethylcyclopentyl]carbonyl}-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate (1.58 g, 4.7 mmol) in dichloromethane (25 ml) was treated with sodium triacetoxyborohydride (2.36 g, 11.1 mmol) and 3R)-3-methoxytetrahydro-4H-pyran-4-one (0.76 g, 7.6 mmol). The reaction was stirred under nitrogen at 0° C. for 30 minutes then allowed to warm to room temperature and stirred for 15 hours. The reaction was treated with 2.5N NaOH (10 mL) and stirred for 10 minutes. The reaction was diluted with water and the layers separated. The aqueous layer was extracted twice with ethyl acetate. The dichloromethane layer was concentrated under reduced pressure and partitioned between ethyl acetate and water. The organic layers were combined, washed with brine, dried over MgSO4, concentrated under reduced pressure and purified with the Biotage (0-100% methanol/ethyl acetate, 15 column volumes) to give the desired product, 1,5-anhydro-3-{[(1R,3S)-3-{[(1S,4S)-5-(tert-butoxycarbonyl)-2,5-diazabicyclo[2.2.1]hept-2-yl]carbonyl}-3-ethylcyclopentyl]amino}-2,3-dideoxy-4-O-methyl-D-erythro-pentitol. LC/MS (M+H)=452.3124 exp, 452.3135 obs; 1H NMR (400 MHz, CDCl3) δ ppm 4.94-4.41 (2H), 4.11-4.04 (1H), 3.97-3.91 (1H), 3.53-3.18 (11H), 2.83-2.75 (1H), 2.60-2.30 (1H), 2.03-1.55 (10H), 1.48-1.37 (11H), 0.85-0.78 (3H)

Provenance & Evidence