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Trifluoroacetic acid → methyl (7S)-14-cyclohexyl-7-({1-[2-(methylamino)ethyl]pyrrolidin-2-yl}methoxy)-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate

HRID 1669452
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1669452
C(O[C:6]([N:8](C)[CH2:9][CH2:10][N:11]1[CH2:15][CH2:14][CH2:13][CH:12]1[CH2:16][O:17][C@H:18]1[CH2:25][N:24]2[C:26]3[CH:27]=[C:28]([C:39]([O:41][CH3:42])=[O:40])[CH:29]=[CH:30][C:31]=3[C:32]([CH:33]3[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]3)=[C:23]2[C:22]2[CH:43]=[CH:44][CH:45]=[CH:46][C:21]=2[O:20][CH2:19]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH:33]1([C:32]2[C:31]3[CH:30]=[CH:29][C:28]([C:39]([O:41][CH3:42])=[O:40])=[CH:27][C:26]=3[N:24]3[C:23]=2[C:22]2[CH:43]=[CH:44][CH:45]=[CH:46][C:21]=2[O:20][CH2:19][C@@H:18]([O:17][CH2:16][CH:12]2[CH2:13][CH2:14][CH2:15][N:11]2[CH2:10][CH2:9][NH:8][CH3:6])[CH2:25]3)[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38]1
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Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 67344077methyl (7S)-7-[(1-{2-[(tert-butoxycarbonyl)(methyl)amino]ethyl}pyrrolidin-2-yl)methoxy]-14-cyclohexyl-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate

Produkt 1

HCID 67344987methyl (7S)-14-cyclohexyl-7-({1-[2-(methylamino)ethyl]pyrrolidin-2-yl}methoxy)-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylateAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344
Dichloromethane
Lösungsmittel

Versuchsvorschrift

A solution of methyl (7S)-7-[(1-{2-[(tert-butoxycarbonyl)(methyl)amino]ethyl}pyrrolidin-2-yl)methoxy]-14-cyclohexyl-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate (0.06 M) in DCM was treated with an excess of TFA (>50 eq). The mixture was stirred at RT for 2 h. Volatiles were removed in vacuo and the residue partitioned between EtOAc and sat. aq. NaHCO3. The aqueous was extracted with EtOAc and the organics combined, washed with brine, dried (Na2SO4), filtered and concentrated in vacuo to afford the product (82%). The material was taken on without further purification. (ES+) m/z 546 (M+H)+.

Aufarbeitung

  1. customVolatiles were removed in vacuo
  2. customthe residue partitioned between EtOAc and sat. aq. NaHCO3
  3. extractionThe aqueous was extracted with EtOAc
  4. washwashed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-3fc2fce0989740569f5fd274b1901b71
Quelldatensatz
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07989438B2

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