Trifluoroacetic acid → (S)-(3,5-bistrifluoromethylbenzyl)-(2-methyl-2H-tetrazol-5-yl)-(7-methyl-8-trifluoromethyl-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl)amine

HRID 507036Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 507036
FC(F)(F)C(O)=O.[F:8][C:9]([F:52])([F:51])[C:10]1[CH:11]=[C:12]([CH:44]=[C:45]([C:47]([F:50])([F:49])[F:48])[CH:46]=1)[CH2:13][N:14]([C:38]1[N:39]=[N:40][N:41]([CH3:43])[N:42]=1)[C@H:15]1[CH2:21][CH2:20][CH2:19][N:18](C(OC(C)(C)C)=O)[C:17]2[CH:29]=[C:30]([C:34]([F:37])([F:36])[F:35])[C:31]([CH3:33])=[CH:32][C:16]1=2.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[F:51][C:9]([F:8])([F:52])[C:10]1[CH:11]=[C:12]([CH:44]=[C:45]([C:47]([F:50])([F:48])[F:49])[CH:46]=1)[CH2:13][N:14]([C:38]1[N:39]=[N:40][N:41]([CH3:43])[N:42]=1)[C@H:15]1[CH2:21][CH2:20][CH2:19][NH:18][C:17]2[CH:29]=[C:30]([C:34]([F:35])([F:36])[F:37])[C:31]([CH3:33])=[CH:32][C:16]1=2

Komponenten

5

Edukt 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 11585492(S)-tert-Butyl 5-[(3,5-bistrifluoromethylbenzyl)-(2-methyl-2H-tetrazol-5-yl)amino]-7-methyl-8-trifluoromethyl-2,3,4,5-tetrahydrobenzo[b]azepine-1-carboxylate

Produkt 1

HCID 59432408(S)-(3,5-bistrifluoromethylbenzyl)-(2-methyl-2H-tetrazol-5-yl)-(7-methyl-8-trifluoromethyl-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl)amineAusbeute 100,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Add trifluoroacetic acid (10 mL) to a solution of (S)-tert-butyl 5-[(3,5-bistrifluoromethylbenzyl)-(2-methyl-2H-tetrazol-5-yl)amino]-7-methyl-8-trifluoromethyl-2,3,4,5-tetrahydrobenzo[b]azepine-1-carboxylate (2.04 g, 3.13 mmol) in methylene chloride (50 mL) at 0° C. under nitrogen. Warm the mixture to room temperature, stir for 8 h and pour the mixture into saturated aqueous sodium bicarbonate solution (200 mL). Extract the mixture with methylene chloride (200 mL) and wash the combined organic extracts with brine (50 mL), dry over anhydrous sodium sulfate and filter. Remove the solvent under reduced pressure to provide the title compound as a colorless oil (1.73 g, >99%), which is used in the next step without purification. APCI MS m/z 553 (M+H)+.

Aufarbeitung

  1. extractionExtract the mixture with methylene chloride (200 mL)
  2. washwash the combined organic extracts with brine (50 mL)
  3. dry with materialdry over anhydrous sodium sulfate
  4. filtrationfilter
  5. customRemove the solvent under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-a5a407774c004243bc449609cc1ba51e
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07786108B2

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