Trifluoroacetic acid → (S)-2-{5-[(3,5-Bis-trifluoromethyl-benzyl)-(7-methyl-8-trifluoromethyl-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl)-amino]-tetrazol-2-yl}-ethanol

HRID 507045Notes

Reaction equation

HRID 507045 reaction equation
FC(F)(F)C(O)=O.C(OC([N:15]1[CH2:21][CH2:20][CH2:19][C@H:18]([N:22]([CH2:31][C:32]2[CH:37]=[C:36]([C:38]([F:41])([F:40])[F:39])[CH:35]=[C:34]([C:42]([F:45])([F:44])[F:43])[CH:33]=2)[C:23]2[N:24]=[N:25][N:26]([CH2:28][CH2:29][OH:30])[N:27]=2)[C:17]2[CH:46]=[C:47]([CH3:54])[C:48]([C:50]([F:53])([F:52])[F:51])=[CH:49][C:16]1=2)=O)(C)(C)C>C(Cl)Cl>[F:44][C:42]([F:43])([F:45])[C:34]1[CH:33]=[C:32]([CH:37]=[C:36]([C:38]([F:41])([F:40])[F:39])[CH:35]=1)[CH2:31][N:22]([C@H:18]1[CH2:19][CH2:20][CH2:21][NH:15][C:16]2[CH:49]=[C:48]([C:50]([F:51])([F:52])[F:53])[C:47]([CH3:54])=[CH:46][C:17]1=2)[C:23]1[N:24]=[N:25][N:26]([CH2:28][CH2:29][OH:30])[N:27]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59432357(S)-5-{(3,5-Bis-trifluoromethyl-benzyl)-(2-(2-hydroxy-ethyl)-2H-tetrazol-5-yl)-amino}-7-methyl-8-trifluoromethyl-2,3,4,5-tetrahydro-benzo[b]azepine-1-carboxylic acid tert-butyl ester

Product 1

HCID 59432306(S)-2-{5-[(3,5-Bis-trifluoromethyl-benzyl)-(7-methyl-8-trifluoromethyl-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl)-amino]-tetrazol-2-yl}-ethanolYield 62%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add trifluoroacetic acid (2 mL) to a solution of (S)-5-{(3,5-Bis-trifluoromethyl-benzyl)-[2-(2-hydroxy-ethyl)-2H-tetrazol-5-yl]-amino}-7-methyl-8-trifluoromethyl-2,3,4,5-tetrahydro-benzo[b]azepine-1-carboxylic acid tert-butyl ester (0.0650 g, 0.0952 mmol) in methylene chloride (2 mL) at room temperature, stir for 1 h. Evaporate solvents and partition the residue between saturated aqueous sodium bicarbonate solution (10 mL). Extract the mixture with methylene chloride (10 mL). Separate two layers and dry over anhydrous sodium sulfate and filter. Remove the solvent under reduced pressure. Chromatograph the residue over silica gel, eluting with ethyl acetate/hexanes (0-100%), to provide the title compound as a colorless oil (0.0340 g, 62%). MS (ES+): 583 (M+H).

Workup

  1. customEvaporate solvents and partition the residue between saturated aqueous sodium bicarbonate solution (10 mL)
  2. extractionExtract the mixture with methylene chloride (10 mL)
  3. customSeparate two layers
  4. dry with materialdry over anhydrous sodium sulfate
  5. filtrationfilter
  6. customRemove the solvent under reduced pressure
  7. washChromatograph the residue over silica gel, eluting with ethyl acetate/hexanes (0-100%)

Sources & evidence

ORD record
ord-efadb55086e9414ab09ec3d266b08c49
Source dataset
uspto-grants-2010_08
Patent number
US07786108B2

Reaction notes

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