HCID 68281563, compound → HCID 68281487, compound

Participants

Reaction Steps

(R)-tert-butyl 1-(1-hydroxy-3,3-dimethyl-1,3-dihydrobenzo[c][1,2]oxaborol-6-ylamino)-1-oxo-4-(4-(trifluoromethyl)phenyl)butan-2-ylcarbamate (1.44 g, 2.844 mmol) was stirred with 4.4 M HCl/EtOAc (10 mL) at room temperature for 30 min. The solution was evaporated to dryness under vacuum to produce (R)-2-amino-N-(1-hydroxy-3,3-dimethyl-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)-4-(4-(trifluoromethyl)phenyl)butanamide (CLXIX) as a light orange solid (1.22 g, 2.75 mmol, 97% yield). 1H NMR (DMSO-d6) δ ppm 1.46 (s, 6H), 2.22-2.29 (m, 2H), 2.83-2.91 (m, 2H), 4.17-4.22 (m, 1H), 7.35 (d, 1H, J=8 Hz), 7.47 (d, 2H, J=8 Hz), 7.62 (d, 2H, J=8 Hz), 7.65-7.68 (m, 1H), 7.92 (s, 1H), 8.53 (brs, 3H), 10.76 (s, 1H); 19F NMR (DMSO-d6) δ ppm −60.17 (s, 3F); ESIMS found for C20H22BF3N2O3 m/z 407.4 (M+H), 405.3 (M−H).

Provenance & Evidence