Sodium bis(trimethylsilyl)amide → N-tert-Butyl-2-(2,4-dioxo-5-phenyl-2,3,4,5-tetrahydro-benzo[b][1,4]diazepin-1-yl)-N-phenyl-acetamide

HRID 343149노트

반응식

HRID 343149 반응식
[C:1]1([N:7]2[C:13](=[O:14])[CH2:12][C:11](=[O:15])[NH:10][C:9]3[CH:16]=[CH:17][CH:18]=[CH:19][C:8]2=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].Br[CH2:31][C:32]([N:34]([C:41]([CH3:44])([CH3:43])[CH3:42])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:33]>CN(C=O)C.C1COCC1>[C:41]([N:34]([C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)[C:32](=[O:33])[CH2:31][N:10]1[C:11](=[O:15])[CH2:12][C:13](=[O:14])[N:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:8]2[CH:19]=[CH:18][CH:17]=[CH:16][C:9]1=2)([CH3:42])([CH3:43])[CH3:44]

참가 물질

6

반응물 3

HCID 2724254Sodium bis(trimethylsilyl)amideHCID 10824683N-Desmethyl Dechloro ClobazamHCID 108258822-Bromo-N-tert-butyl-N-phenyl-acetamide

생성물 1

HCID 10789281N-tert-Butyl-2-(2,4-dioxo-5-phenyl-2,3,4,5-tetrahydro-benzo[b][1,4]diazepin-1-yl)-N-phenyl-acetamide수율 71%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매2회HCID 8028Tetrahydrofuran용매

실험 절차

To a stirred solution of 600 mg (2.38 mmol) 1-Phenyl-2,3,4,5-tetrahydro-benzo[b][1,4]diazepin-2,4-dione in 16 mL DMF is added 2.62 mL (2.62 mmol, 1.1 equiv) of 1M Sodium bis(trimethylsilyl)amide in THF at ambient temperature and stirred 0.5 h. To this solution is added 707 mg (2.62 mmol, 1.1 equiv) 2-Bromo-N-tert-butyl-N-phenyl-acetamide, prepared as in Part A, in 4 mL DMF and stirred 18 h at ambient temperature. The solvent is removed in vacuo and the residue taken into 50 mL EtOAc, washed successively with H2O (30 mL), 1N HCl (30 mL), satd. NaHCO3 (30 mL), and brine (30 mL), dried (MgSO4), filtered and concentrated in vacuo to a brown oil. The crude product is purified by flash chromatography on 40 g silica gel eluted successively with EtOAc/Hexanes (2:3, 500 mL), (1:1, 750 mL). Appropriate fractions were combined and concentrated in vacuo to give 748 mg (1.69 mmol) of N-tert-Butyl-2-(2,4-dioxo-5-phenyl-2,3,4,5,-tetrahydro-benzo[b][1,4]diazepin-1-yl)-N-phenyl-acetamide as a white foam: 1H NMR (CDCl3, 300 MHz) δ7.45-7.21 (m, 12H), 7.08 (t, 1H), 6.90 (m, 1H), 4.30 (d, 1H, J=16.4), 3.85 (d, 1H, J=16.6), 3.59 (d, 1H, J=12.0), 3.49 (d, 1H, J=11.9), 1.43 (s, 9H); TLC Rf =0.24 (EtOAc/Hexanes, 1:1).

후처리

  1. additionTo this solution is added
  2. customThe solvent is removed in vacuo
  3. washwashed successively with H2O (30 mL), 1N HCl (30 mL)
  4. dry with materialNaHCO3 (30 mL), and brine (30 mL), dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo to a brown oil
  7. customThe crude product is purified by flash chromatography on 40 g silica gel
  8. washeluted successively with EtOAc/Hexanes (2:3, 500 mL), (1:1, 750 mL)
  9. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-4254d212a29946edaf673db7300c3acb
출처 데이터셋
uspto-grants-1999_01
특허 번호
US05859007

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