[CH2:1]([O:8][C:9](=[O:15])[NH:10][C@@H:11]([C:13]#[N:14])[CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH2:17][OH:18].C(N(CC)CC)C>C(O)C>[CH2:1]([O:8][C:9](=[O:15])[NH:10][C@H:11]([CH3:12])/[C:13](/[NH2:14])=[N:17]/[OH:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1To a solution of benzyl[(1R)-1-cyanoethyl]carbamate (2.52 g, 12.3 mmol) in ethanol (30 ml) was added hydroxylamine hydrochloride salt (0.90 g, 13.0 mmol) and triethylamine (3.43 ml, 24.6 mmol) and the mixture heated to 75° C. After 16 h, the solution was concentrated and the residue was dissolved in 200 mL of dichloromethane. The mixture was washed with 100 mL of saturated aqueous sodium bicarbonate (2×) and brine (100 mL). The combined organic extracts were dried over sodium sulfate, filtered and concentrated to give benzyl[(1R,2Z)-2-amino-2-(hydroxyimino)-1-methylethyl]carbamate (2.9 g). MS 238.2 (M+1).
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