Hydrochloric Acid → [Rac]-[2-(3-methoxy-propyl)-4-(methyl-{1-[2-methyl-6-(3-trifluoromethyl-phenyl)-pyridin-3-yl]-butyl}-amino)-phenoxy]-acetic acid

HRID 1242296Notes

Reaction equation

HRID 1242296 reaction equation
C([O:3][C:4](=[O:41])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]([CH3:35])[CH:14]([C:18]2[C:19]([CH3:34])=[N:20][C:21]([C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:33])([F:32])[F:31])[CH:25]=3)=[CH:22][CH:23]=2)[CH2:15][CH2:16][CH3:17])=[CH:9][C:8]=1[CH2:36][CH2:37][CH2:38][O:39][CH3:40])C.[OH-].[Na+].Cl>C1COCC1.CCO>[CH3:40][O:39][CH2:38][CH2:37][CH2:36][C:8]1[CH:9]=[C:10]([N:13]([CH3:35])[CH:14]([C:18]2[C:19]([CH3:34])=[N:20][C:21]([C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:33])([F:32])[F:31])[CH:25]=3)=[CH:22][CH:23]=2)[CH2:15][CH2:16][CH3:17])[CH:11]=[CH:12][C:7]=1[O:6][CH2:5][C:4]([OH:41])=[O:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 670723052-(3-Methoxy-propyl)-4-(methyl-{1-[2-methyl-6-(3-trifluoromethyl-phenyl)-pyridin-3-yl]-butyl}-amino)-phenoxy-acetic acid ethyl ester

Product 1

HCID 21935742[Rac]-[2-(3-methoxy-propyl)-4-(methyl-{1-[2-methyl-6-(3-trifluoromethyl-phenyl)-pyridin-3-yl]-butyl}-amino)-phenoxy]-acetic acid

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

0.082 g (0.143 mmol) of the above prepared [rac]-[2-(3-methoxy-propyl)-4-(methyl-{1-[2-methyl-6-(3-trifluoromethyl-phenyl)-pyridin-3-yl]-butyl}-amino)-phenoxy]-acetic acid ethyl ester was dissolved in 1.64 ml of THF/EtOH=1/1, treated at 0° C. with 0.43 ml (3 eq.) of 1N NaOH, and kept at ambient temperature for 2 h. The reaction mixture was then neutralized with HCl dil. to pH 7, extracted with AcOEt, the organic layer was washed with water, dried over sodium sulfate, and evaporated to dryness to leave 0.070 g of the title compound as light brown oil.

Workup

  1. extractionextracted with AcOEt
  2. washthe organic layer was washed with water
  3. dry with materialdried over sodium sulfate
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-4d553663a3dd46b7a8baeb51a37c2292
Source dataset
uspto-grants-2006_10
Patent number
US07115611B2

Reaction notes

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