HCID 86615656, compound → HCID 11520462, compound

HRID 507046Notes

Reaction equation

HRID 507046 reaction equation
C([O:8][C:9](=[O:56])[CH2:10][CH:11]1[CH2:16][CH2:15][CH:14]([CH2:17][N:18]2[CH2:24][CH2:23][CH2:22][CH:21]([N:25]([CH2:32][C:33]3[CH:38]=[C:37]([C:39]([F:42])([F:41])[F:40])[CH:36]=[C:35]([C:43]([F:46])([F:45])[F:44])[CH:34]=3)[C:26]3[N:27]=[N:28][N:29]([CH3:31])[N:30]=3)[C:20]3[CH:47]=[C:48]([CH3:55])[C:49]([C:51]([F:54])([F:53])[F:52])=[CH:50][C:19]2=3)[CH2:13][CH2:12]1)C1C=CC=CC=1>[OH-].[Na+].CO>[F:45][C:43]([F:44])([F:46])[C:35]1[CH:34]=[C:33]([CH:38]=[C:37]([C:39]([F:42])([F:41])[F:40])[CH:36]=1)[CH2:32][N:25]([C:26]1[N:27]=[N:28][N:29]([CH3:31])[N:30]=1)[CH:21]1[CH2:22][CH2:23][CH2:24][N:18]([CH2:17][CH:14]2[CH2:15][CH2:16][CH:11]([CH2:10][C:9]([OH:56])=[O:8])[CH2:12][CH2:13]2)[C:19]2[CH:50]=[C:49]([C:51]([F:52])([F:53])[F:54])[C:48]([CH3:55])=[CH:47][C:20]1=2

Participants

4

Reactant 1

HCID 86615656HCID 86615656, compound

Product 1

HCID 11520462HCID 11520462, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

Heat the mixture of (4-{5-[(3,5-Bis-trifluoromethyl-benzyl)-(2-methyl-2H-tetrazol-5-yl)-amino]-7-methyl-8-trifluoromethyl-2,3,4,5-tetrahydro-benzo[b]azepin-1-ylmethyl}-cyclohexyl)-acetic acid benzyl ester (0.0340 g, 0.0427 mmol) in 5.0 N NaOH (1 mL) and methanol (1 mL) at 60° C. for 2 h. Evaporate the solvents and re-dissolve in water (10 mL). Adjust to pH=2 by adding 5.0 N HCl. Extract with ethyl acetate (2×10 mL). Combine 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 (0-50%), to provide the title compound as a colorless oil (0.0200 g, 67%). MS (ES+): MS (ES+): 707 (M+H).

Workup

  1. temperatureHeat
  2. customEvaporate the solvents
  3. dissolutionre-dissolve in water (10 mL)
  4. additionby adding 5.0 N HCl
  5. extractionExtract with ethyl acetate (2×10 mL)
  6. dry with materialCombine organic layers, dry over anhydrous sodium sulfate
  7. filtrationfilter
  8. customRemove the solvent under reduced pressure
  9. washChromatograph the residue over silica gel, eluting with ethyl acetate/hexanes (0-50%)

Sources & evidence

ORD record
ord-4df319fd3670489393f1d55b8f2a10a5
Source dataset
uspto-grants-2010_08
Patent number
US07786108B2

Reaction notes

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