[C:1]([O:5][C:6](=[O:18])[NH:7][CH2:8][C:9]1([C:15](=O)[NH2:16])[CH2:11][CH:10]1[CH:12]([CH3:14])[CH3:13])([CH3:4])([CH3:3])[CH3:2].N1C(Cl)=NC(Cl)=NC=1Cl.[OH-].[Na+]>CN(C=O)C>[C:1]([O:5][C:6](=[O:18])[NH:7][CH2:8][C:9]1([C:15]#[N:16])[CH2:11][CH:10]1[CH:12]([CH3:13])[CH3:14])([CH3:2])([CH3:4])[CH3:3]To a solution of (1-carbamoyl-2-isopropyl-cyclopropylmethyl)-carbamic acid tert-butyl ester (6.4 g, 24.9 mmol) in dry DMF (100 mL) was added cyanuric chloride (6.4 g, 34.9 mmol). The reaction mixture was stirred at 0° C. for 30 minutes and was poured into cold 0.5N NaOH (200 mL). The aqueous phase was extracted with EtOAc (2×150 mL) and the combined organic layer was washed with water and brine and dried over Na2SO4. Removal of excess of solvent, followed by purification of the residue by flash column chromatography using hexanes/EtOAc (9:1) as eluent gave 4.4 g (74%) of (1-cyano-2-isopropyl-cyclopropylmethyl)-carbamic acid tert-butyl ester as a colorless foam: 1H NMR (300 MHz, CDCl3) δ 0.87 (m, 1H), 1.05 (s, 6H), 1.23-1.33 (m, 3H), 1.45 (s, 9H), 3.29 (dd, J=6.3, 14.5 Hz, 1H), 3.47 (dd, J=6.1, 14.6 Hz, 1H), 5.31 (m, 1H); 13C NMR (75 MHz, CDCl3) δ 14.6, 16.9, 21.0, 21.3, 27.1, 33.3, 39.3, 78.5, 122.0, 154.6; MS (APCI) m/z 239 [M+H]+.
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