Potassium Hydroxide → N-tert-Butyl-2-{3-[tert.-butoxycarbonylamino]-8-methyl-2-oxo-5-phenyl-1,3,4,5-tetrahydro-benzo[b]azepin-1-yl}-acetamide

HRID 1601657노트

반응식

HRID 1601657 반응식
[C:1]([O:5][C:6]([NH:8][CH:9]1[C:15](=[O:16])[NH:14][C:13]2[CH:17]=[C:18]([CH3:21])[CH:19]=[CH:20][C:12]=2[CH:11]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:28]([NH:32][C:33](=[O:36])[CH2:34]I)([CH3:31])([CH3:30])[CH3:29].[OH-].[K+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1.C(OCC)(=O)C>[C:28]([NH:32][C:33](=[O:36])[CH2:34][N:14]1[C:15](=[O:16])[CH:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:10][CH:11]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:12]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][C:13]1=2)([CH3:31])([CH3:30])[CH3:29]

참가 물질

7

반응물 3

HCID 14797Potassium HydroxideHCID 13501613N-(Tert-butyl)-2-iodoacetamideHCID 570632293-[Tert.-butoxycarbonylamino]-8-methyl-2-oxo-5-phenyl-1,3,4,5-tetrahydro-benzo[b]azepine

생성물 1

HCID 57277227N-tert-Butyl-2-{3-[tert.-butoxycarbonylamino]-8-methyl-2-oxo-5-phenyl-1,3,4,5-tetrahydro-benzo[b]azepin-1-yl}-acetamide수율 100%

시약·촉매·용매 3

HCID 74236Tetrabutylammonium Bromide촉매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

3-[Tert.-butoxycarbonylamino]-8-methyl-2-oxo-5-phenyl-1,3,4,5-tetrahydro-benzo[b]azepine (1.4 g, 3.8 mmol), N-t-butyl iodoacetamide (1.1 g, 4.56 mmol) and tetrabutylammonium bromide (85 mg, 0.26 mmol) were dissolved in dry tetrahydrofuran (25 ml) under nitrogen. Powder potassium hydroxide (0.3 g, 4.5 mmol) was added in one portion and the reaction was stirred for 5 hours. The reaction was diluted with ethyl acetate (25 ml) and washed with water (2×50 ml) and brine. After drying over magnesium sulfate, the solvent was evaporated in vacuo to provide the desired product as a foam; 2 g, >100% yield. This contained some excess iodoacetamide, but was suitable for use in the next reaction. IR (KBr) 1720, 1680, 1659, 1614 cm-1. 1H NMR (CDCl3) δ 7.28-7.07 (m, 6), 7.00 (d, 2), 6.05 (s, 1), 5.49 (d, 1), 4.34 (m, 1), 4.08 (d, 1), 3.62 (d, 1), 2.95 (dt, 1), 2.63 (t, 1), 2.60 (d, 1), 2.33 (s, 3), 1.41 (s, 9), 1.32 (s, 9).

후처리

  1. washwashed with water (2×50 ml) and brine
  2. dry with materialAfter drying over magnesium sulfate
  3. customthe solvent was evaporated in vacuo

출처 및 근거

ORD 기록
ord-ed82705f4d5842ae93dd9abe0bc32d05
출처 데이터셋
uspto-grants-1999_11
특허 번호
US05977355

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