Hydrochloric Acid → 3-{3-Chloro-5-(methyloxy)-4-[((1S)-1-{6-[4-(trifluoromethyl)phenyl]-2-pyridinyl}pentyl)oxy]phenyl}propanoic acid

HRID 1391820Notes

Reaction equation

HRID 1391820 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:32][CH2:33][C:34]([O:36]CC)=[O:35])[CH:5]=[C:6]([O:30][CH3:31])[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].[OH-].[Na+].Cl>C1COCC1.CO>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:32][CH2:33][C:34]([OH:36])=[O:35])[CH:5]=[C:6]([O:30][CH3:31])[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:27])[F:28])=[CH:22][CH:21]=2)[N:15]=1)[CH2:10][CH2:11][CH2:12][CH3:13]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 58629932Ethyl 3-{3-chloro-5-(methyloxy)-4-[((1S)-1-{6-[4-(trifluoromethyl)phenyl]-2-pyridinyl}pentyl)oxy]phenyl}propanoate

Product 1

HCID 102561863-{3-Chloro-5-(methyloxy)-4-[((1S)-1-{6-[4-(trifluoromethyl)phenyl]-2-pyridinyl}pentyl)oxy]phenyl}propanoic acidYield 90%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirring solution of ethyl 3-{3-chloro-5-(methyloxy)-4-[((1S)-1-{6-[4-(trifluoromethyl)phenyl]-2-pyridinyl}pentyl)oxy]phenyl}propanoate (118 mg, 0.20 mmol) in THF (3 mL) and MeOH (3 mL) at ambient temperature was added NaOH (2N, 3 mL) and the mixture stirred for 2 h and then left to stand overnight. HCl (2N, 3 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 the title compound (94 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-1c63796dc72d41c9b1337fbd980a1094
Source dataset
uspto-grants-2008_03
Patent number
US07338960B2

Reaction notes

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