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 1601657Notes

Reaction equation

HRID 1601657 reaction equation
[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]

Participants

7

Reactant 3

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

Product 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}-acetamideYield 100%

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-ed82705f4d5842ae93dd9abe0bc32d05
Source dataset
uspto-grants-1999_11
Patent number
US05977355

Reaction notes

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