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 1601657Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1601657
[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]

Komponenten

7

Edukt 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

Produkt 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}-acetamideAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 74236Tetrabutylammonium BromideKatalysatorHCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-ed82705f4d5842ae93dd9abe0bc32d05
Quelldatensatz
uspto-grants-1999_11
Patentnummer
US05977355

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