HCID 86615667, compound → HCID 86615666, compound

HRID 507161Notes

Reaction equation

HRID 507161 reaction equation
C[O:2][C:3](=[O:51])[CH2:4][CH:5]1[CH2:10][CH2:9][CH:8]([CH2:11][N:12]2[CH2:18][CH2:17][CH2:16][C@H:15]([N:19]([CH2:26][C:27]3[CH:32]=[C:31]([C:33]([F:36])([F:35])[F:34])[CH:30]=[C:29]([C:37]([F:40])([F:39])[F:38])[CH:28]=3)[C:20]3[N:21]=[N:22][N:23]([CH3:25])[N:24]=3)[C:14]3[CH:41]=[C:42]([CH3:50])[C:43]([C:46]([F:49])([F:48])[F:47])=[C:44]([CH3:45])[C:13]2=3)[CH2:7][CH2:6]1>[OH-].[Na+].CO>[F:39][C:37]([F:38])([F:40])[C:29]1[CH:28]=[C:27]([CH:32]=[C:31]([C:33]([F:36])([F:35])[F:34])[CH:30]=1)[CH2:26][N:19]([C:20]1[N:21]=[N:22][N:23]([CH3:25])[N:24]=1)[C@H:15]1[CH2:16][CH2:17][CH2:18][N:12]([CH2:11][CH:8]2[CH2:9][CH2:10][CH:5]([CH2:4][C:3]([OH:51])=[O:2])[CH2:6][CH2:7]2)[C:13]2[C:44]([CH3:45])=[C:43]([C:46]([F:47])([F:48])[F:49])[C:42]([CH3:50])=[CH:41][C:14]1=2

Participants

4

Reactant 1

HCID 86615667HCID 86615667, compound

Product 1

HCID 86615666HCID 86615666, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

Heat the mixture of (S)-(4-{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-ylmethyl}-cyclohexyl)-acetic acid methyl ester (0.0950 g, 0.129 mmol) in 5.0 N NaOH (1 mL) and methanol (2 mL) under reflux for 2 h. Evaporate the solvents and re-dissolve in water (10 mL). Adjust to pH=7 by adding 2.0 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 (0-100%), to provide the title compound as a white foam (0.0620 g, 67%). MS (ES+): 721 (M+H); 719 (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 2.0 N HCl
  6. extractionExtract with ethyl acetate (2×10 mL)
  7. dry with materialCombine 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-1e2b4861d248407bb0e51f6782380c5a
Source dataset
uspto-grants-2010_08
Patent number
US07786108B2

Reaction notes

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