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 1601657ノート

反応式

HRID 1601657 の反応式
[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]

参加物

7

反応物 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

生成物 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}-acetamide収率 100%

試薬・触媒・溶媒 3

HCID 74236Tetrabutylammonium Bromide触媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-ed82705f4d5842ae93dd9abe0bc32d05
出典データセット
uspto-grants-1999_11
特許番号
US05977355

反応ノート

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