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

HRID 507115Notes

Reaction equation

HRID 507115 reaction equation
FC(F)(F)C(O)=O.C(OC([N:15]1[CH2:21][CH2:20][CH2:19][C@H:18]([N:22]([CH2:29][C:30]2[CH:35]=[C:34]([C:36]([F:39])([F:38])[F:37])[CH:33]=[C:32]([C:40]([F:43])([F:42])[F:41])[CH:31]=2)[C:23]2[O:27][N:26]=[C:25]([CH3:28])[CH:24]=2)[C:17]2[CH:44]=[C:45]([CH3:52])[C:46]([C:48]([F:51])([F:50])[F:49])=[CH:47][C:16]1=2)=O)(C)(C)C.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[F:43][C:40]([F:41])([F:42])[C:32]1[CH:31]=[C:30]([CH:35]=[C:34]([C:36]([F:39])([F:38])[F:37])[CH:33]=1)[CH2:29][N:22]([C:23]1[O:27][N:26]=[C:25]([CH3:28])[CH:24]=1)[C@H:18]1[CH2:19][CH2:20][CH2:21][NH:15][C:16]2[CH:47]=[C:46]([C:48]([F:51])([F:49])[F:50])[C:45]([CH3:52])=[CH:44][C:17]1=2

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 59432319(S)-5-[(3,5-Bis-trifluoromethyl-benzyl)-(3-methyl-isoxazol-5-yl)-amino]-7-methyl-8-trifluoromethyl-2,3,4,5-tetrahydro-benzo[b]azepine-1-carboxylic acid tert-butyl ester

Product 1

HCID 59432390(S)-(3,5-Bis-trifluoromethyl-benzyl)-(3-methyl-isoxazol-5-yl)-(7-methyl-8-trifluoromethyl-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl)-amineYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add trifluoroacetic acid (10 mL) to a solution of (S)-5-[(3,5-bis-trifluoromethyl-benzyl)-(3-methyl-isoxazol-5-yl)-amino]-7-methyl-8-trifluoromethyl-2,3,4,5-tetrahydro-benzo[b]azepine-1-carboxylic acid tert-butyl ester (140 mg, 0.458 mmol) in methylene chloride (5 mL) at 0° C. under nitrogen. Warm the mixture to room temperature, stir for 4 h and pour the mixture into saturated aqueous sodium bicarbonate solution (20 mL). Extract the mixture with methylene chloride (20 mL) and wash the combined organic extracts with brine (10 mL), dry over anhydrous sodium sulfate and filter. Remove the solvent under reduced pressure to provide the title compound as a colorless oil (90 mg, 76%), which is used in the next step without purification: ESI MS m/z 552 [C25H22F9N3O+H]+.

Workup

  1. extractionExtract the mixture with methylene chloride (20 mL)
  2. washwash the combined organic extracts with brine (10 mL)
  3. dry with materialdry over anhydrous sodium sulfate
  4. filtrationfilter
  5. customRemove the solvent under reduced pressure

Sources & evidence

ORD record
ord-c893cb5aae8649249c3ccc6c83bad57d
Source dataset
uspto-grants-2010_08
Patent number
US07786108B2

Reaction notes

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