Trifluoroacetic acid → 13-cyclohexyl-3-methoxy-6-(methoxycarbonyl)-7H-indolo[2,1-a][2]benzazepine-10-carboxylic acid

HRID 1091558Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1091558
FC(F)(F)C(O)=O.[CH:8]1([C:14]2[C:15]3[CH:16]=[CH:17][C:18]([C:38]([O:40]C(C)(C)C)=[O:39])=[CH:19][C:20]=3[N:21]3[CH2:27][C:26]([C:28]([O:30][CH3:31])=[O:29])=[CH:25][C:24]4[CH:32]=[C:33]([O:36][CH3:37])[CH:34]=[CH:35][C:23]=4[C:22]=23)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1>ClC(Cl)C>[CH:8]1([C:14]2[C:15]3[CH:16]=[CH:17][C:18]([C:38]([OH:40])=[O:39])=[CH:19][C:20]=3[N:21]3[CH2:27][C:26]([C:28]([O:30][CH3:31])=[O:29])=[CH:25][C:24]4[CH:32]=[C:33]([O:36][CH3:37])[CH:34]=[CH:35][C:23]=4[C:22]=23)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 5983755810-tert-butyl 6-methyl 13-cyclohexyl-3-methoxy-7H-indolo[2,1-a][2]benzazepine-6,10-dicarboxylate

Produkt 1

HCID 5755909813-cyclohexyl-3-methoxy-6-(methoxycarbonyl)-7H-indolo[2,1-a][2]benzazepine-10-carboxylic acidAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 63651,1-DichloroethaneLösungsmittel

Versuchsvorschrift

Trifluoroacetic acid (30 mL) was added dropwise to a stirring slurry of 10-tert-butyl 6-methyl 13-cyclohexyl-3-methoxy-7H-indolo[2,1-a][2]benzazepine-6,10-dicarboxylate (10 g, 20 mmol) in dichloroethane (30 mL) under N2. The clear dark green solution was stirred at rt for 2.5 h, concentrated to dryness and stirred with EtOAc (100 mL) overnight. The solids were collected by filtration, washed with EtOAc and Et2O to yield 13-cyclohexyl-3-methoxy-6-(methoxycarbonyl)-7H-indolo[2,1-a][2]benzazepine-10-carboxylic acid (8.35 g, 18.8 mmol, 94%) was as a yellow solid which was used without further purification. 1H NMR (300 MHz, CDCl3) δ 1.13-2.16 (m, 10H), 2.74-2.88 (m, 1H), 3.84 (s, 3H), 3.89 (s, 3H), 4.06-4.29 (m, 1H), 5.54-5.76 (m, 1H), 6.98 (d, J=2.6 Hz, 1H), 7.08 (dd, J=8.4, 2.6 Hz, 1H), 7.52 (d, J=8.4 Hz, 1H), 7.78 (dd, J=8.8, 1.1 Hz, 1H), 7.80 (s, 1H), 7.86 (d, J=8.8 Hz, 1H), 8.34 (d, J=1.1 Hz, 1H). LCMS: m/e 446 (M+H)+, ret time 3.21 min, column B, 4 minute gradient.

Aufarbeitung

  1. concentrationconcentrated to dryness
  2. stirringstirred with EtOAc (100 mL) overnight
  3. filtrationThe solids were collected by filtration
  4. washwashed with EtOAc and Et2O

Quellen und Nachweise

ORD-Eintrag
ord-153b04f356e1416a804303f8b1189316
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08129367B2

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