Hydrochloric Acid → HCID 69212227, compound

HRID 1391821Notes

Reaction equation

HRID 1391821 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4](/[CH:30]=[CH:31]/[C:32]([O:34]CC)=[O:33])[CH:5]=[CH:6][C:7]=1[O:8][C@@H: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].CO.[OH-].[Na+].Cl>CCOC(C)=O.C1COCC1.O=[Pt]=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:30][CH2:31][C:32]([OH:34])=[O:33])[CH:5]=[CH:6][C:7]=1[O:8][C@@H:9]([C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([C:20]2[CH:21]=[CH:22][C:23]([C:26]([F:28])([F:29])[F:27])=[CH:24][CH:25]=2)[N:15]=1)[CH2:10][CH2:11][CH2:12][CH3:13]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 86604666HCID 86604666, compound

Product 1

HCID 69212227HCID 69212227, compoundYield 61%

Reagents, catalysts & solvents 3

HCID 345198Adams' catalystCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirring solution of ethyl (2E)-3-{3-chloro-4-[((1R)-1-{6-[4-(trifluoromethyl)phenyl]-2-pyridinyl}pentyl)oxy]phenyl}-2-propenoate (54 mg, 0.10 mmol) in EtOAc (4 mL) under nitrogen at ambient temperature was added PtO2 (20 wt %, 11 mg) and the mixture stirred under an atmosphere of hydrogen for 5 h. The resulting mixture was then purified by SPE (silica, 5 g cartridge) with a pad of celite on the top, eluting with EtOAc. The filtrate was then reduced and purified further by SPE (silica, 5 g cartridge) eluting with cyclohexane:EtOAc (gradient 50:1 to 20:1) to give an inseparable mixture containing the desired material and some de -chlorinated compound (51 mg). This material was then dissolved in THF (2 mL) and MeOH (2 mL) at ambient temperature and treated with NaOH (2N, 2 mL). The resulting mixture was then stirred for 2 h and then left to stand overnight. HCl (2N, 2 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 20:1 to 0:1) to give a residue which was purified further by mass directed autoprep HPLC to give the title compound (30 mg).

Workup

  1. customThe resulting mixture was then purified by SPE (silica, 5 g cartridge) with a pad of celite on the top
  2. washeluting with EtOAc
  3. custompurified further by SPE (silica, 5 g cartridge)
  4. washeluting with cyclohexane
  5. customEtOAc (gradient 50:1 to 20:1) to give an inseparable mixture
  6. stirringThe resulting mixture was then stirred for 2 h
  7. waitleft
  8. waitto stand overnight
  9. customThe residue was then purified by SPE (silica, 5 g cartridge) with a pad of celite on the top
  10. washeluting with cyclohexane
  11. customEtOAc (gradient 20:1 to 0:1) to give a residue which
  12. customwas purified further by mass

Sources & evidence

ORD record
ord-3b2cb60f99a145fd89508e22ea5dc484
Source dataset
uspto-grants-2008_03
Patent number
US07338960B2

Reaction notes

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