2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile → HCID 10267278、化合物
反応式
[CH3:1][C:2]([O:5][C:6](ON=C(C1C=CC=CC=1)C#N)=[O:7])([CH3:4])[CH3:3].Cl.Cl.[CH2:21]([O:28][NH:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][NH2:35])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C1COCC1>[CH2:21]([O:28][NH:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][NH:35][C:6]([O:5][C:2]([CH3:4])([CH3:3])[CH3:1])=[O:7])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1参加物
4
実験手順
1 N NaOH (100 mL) was added to (6) (6.01 g, 21.4 mmol), followed by extraction with ether (5×50 mL). After a brine wash (50 mL), solvent was removed to give 4.39 g of (6) as the free amine. BOC-ON (5.10 g, 20.7 mmol ) in distilled THF (100 mL) was added to (6) (free amine, 21.1 mmol) in THF (165 mL) at 0° C. over 30 minutes. The reaction was stirred (0° C. to room temperature) for 24 hours and concentrated in vacuo. Cold 1N NaOH (100 mL) was added, followed by extraction with EtOAc (4×100 mL). The organic layer was washed with cold 1 N NaOH (3×80 mL), cold 0.5M citric acid (100 mL) and brine (2×100 mL). Removal of solvent gave 6.38 g (quantitative) of (7), which was used directly in the next step, as a liquid: NMR δ 1.2-1.7 (m+s, 15 H), 2.66-3.23 (m, 4 H), 4.5 (br s, 1 H), 4.67 (s, 2 H), 7.16-7.34 (m, 5 H) . An analytical sample was purified on a silica gel column, eluting with 15% EtOAc/CHCl3. Anal. calcd. for C17H28N2O3 : C, 66.20; H, 9.15; N, 9.08. Found: C, 66.13; H, 9.10; N, 9.05.