Hydrochloric Acid → HCID 58629851, compound

HRID 1391785Notes

Reaction equation

HRID 1391785 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4](/[CH:31]=[CH:32]/[C:33]([O:35]CC)=[O:34])[CH:5]=[C:6]([CH3:30])[C:7]=1[O:8][CH:9]([C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([C:20]2[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=2)[N:15]=1)[CH2:10][CH2:11][CH2:12][CH3:13].[OH-].[Na+].Cl>C1COCC1.CO>[CH3:30][C:6]1[CH:5]=[C:4](/[CH:31]=[CH:32]/[C:33]([OH:35])=[O:34])[CH:3]=[C:2]([CH3:1])[C:7]=1[O:8][CH:9]([C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([C:20]2[CH:21]=[CH:22][C:23]([C:26]([F:29])([F:27])[F:28])=[CH:24][CH:25]=2)[N:15]=1)[CH2:10][CH2:11][CH2:12][CH3:13]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 58629891HCID 58629891, compound

Product 1

HCID 58629851HCID 58629851, compoundYield 82.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirring solution of ethyl (2E)-3-{3,5-dimethyl-4-[(1-{6-[4-(trifluoromethyl)phenyl]-2-pyridinyl}pentyl)oxy]phenyl}-2-propenoate (35 mg, 0.07 mmol) in THF (5 mL) and MeOH (5 mL) at ambient temperature was added NaOH (2N, 5 mL) and the mixture stirred for 2 h and then left to stand overnight. HCl (2N, 5 mL) was then added and the mixture reduced under vacuum. The residue was then purified by SPE (silica, 5 g cartridge) with a pad of celite on the top, eluting with cyclohexane:EtOAc (gradient 3:1 to 0:1) the EtOAc:MeOH (gradient 95:5 to 0:1) to give the title compound (28 mg).

Workup

  1. waitleft
  2. waitto stand overnight
  3. customThe residue was then purified by SPE (silica, 5 g cartridge) with a pad of celite on the top
  4. washeluting with cyclohexane

Sources & evidence

ORD record
ord-f4163d2c0d8b407da104a203b8070fcc
Source dataset
uspto-grants-2008_03
Patent number
US07338960B2

Reaction notes

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