HCID 86615669, compound → HCID 86615668, compound

HRID 507162Notes

Reaction equation

HRID 507162 reaction equation
C[O:2][C:3](=[O:49])[CH2:4][C:5]([CH3:48])([CH3:47])[CH2:6][CH2:7][N:8]1[CH2:14][CH2:13][CH2:12][C@H:11]([N:15]([CH2:22][C:23]2[CH:28]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:26]=[C:25]([C:33]([F:36])([F:35])[F:34])[CH:24]=2)[C:16]2[N:17]=[N:18][N:19]([CH3:21])[N:20]=2)[C:10]2[CH:37]=[C:38]([CH3:46])[C:39]([C:42]([F:45])([F:44])[F:43])=[C:40]([CH3:41])[C:9]1=2>[OH-].[Na+].CO>[F:31][C:29]([F:30])([F:32])[C:27]1[CH:28]=[C:23]([CH:24]=[C:25]([C:33]([F:36])([F:35])[F:34])[CH:26]=1)[CH2:22][N:15]([C:16]1[N:17]=[N:18][N:19]([CH3:21])[N:20]=1)[C@H:11]1[CH2:12][CH2:13][CH2:14][N:8]([CH2:7][CH2:6][C:5]([CH3:47])([CH3:48])[CH2:4][C:3]([OH:49])=[O:2])[C:9]2[C:40]([CH3:41])=[C:39]([C:42]([F:43])([F:44])[F:45])[C:38]([CH3:46])=[CH:37][C:10]1=2

Participants

4

Reactant 1

HCID 86615669HCID 86615669, compound

Product 1

HCID 86615668HCID 86615668, compoundYield 88.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

Heat the mixture of (S)-5-{5-[(3,5-Bis-trifluoromethyl-benzyl)-(2-methyl-2H-tetrazol-5-yl)-amino]-7,9-dimethyl-8-trifluoromethyl-2,3,4,5-tetrahydro-benzo[b]azepin-1-yl}-3,3-dimethyl-pentanoic acid methyl ester (0.120 g, 0.169 mmol) in 5.0 N NaOH (1 mL) and methanol (5 mL) under reflux for 2 h. Evaporate the solvents and re-dissolve in water (10 mL). Adjust to pH=4 by adding 4.0 N HCl. Extract with ethyl acetate (2×10 mL). Combine the organic layers, 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 white foam (0.104 g, 88%). MS (ES+): 695 (M+H); 693 (M−H).

Workup

  1. temperatureHeat
  2. temperatureunder reflux for 2 h
  3. customEvaporate the solvents
  4. dissolutionre-dissolve in water (10 mL)
  5. additionby adding 4.0 N HCl
  6. extractionExtract with ethyl acetate (2×10 mL)
  7. dry with materialCombine the organic layers, dry over anhydrous sodium sulfate
  8. filtrationfilter
  9. customRemove the solvent under reduced pressure
  10. washChromatograph the residue over silica gel, eluting with ethyl acetate/hexanes (0-100%)

Sources & evidence

ORD record
ord-a091cd18ad2d4407862038a1170ed772
Source dataset
uspto-grants-2010_08
Patent number
US07786108B2

Reaction notes

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