Hydrochloric Acid → 3-Cyclopropyl-3-(6-((5-(2,2-dimethylpropoxy)-6-(2-fluoro-5-methoxyphenyl)pyridin-3-yl)methoxy)pyrimidin-4-yl)propanoic acid

HRID 709792Notes

Reaction equation

HRID 709792 reaction equation
[CH:1]1([CH:4]([C:11]2[CH:16]=[C:15]([O:17][CH2:18][C:19]3[CH:20]=[N:21][C:22]([C:31]4[CH:36]=[C:35]([O:37][CH3:38])[CH:34]=[CH:33][C:32]=4[F:39])=[C:23]([O:25][CH2:26][C:27]([CH3:30])([CH3:29])[CH3:28])[CH:24]=3)[N:14]=[CH:13][N:12]=2)[CH2:5][C:6]([O:8]CC)=[O:7])[CH2:3][CH2:2]1.[OH-].[Na+].Cl>CO>[CH:1]1([CH:4]([C:11]2[CH:16]=[C:15]([O:17][CH2:18][C:19]3[CH:20]=[N:21][C:22]([C:31]4[CH:36]=[C:35]([O:37][CH3:38])[CH:34]=[CH:33][C:32]=4[F:39])=[C:23]([O:25][CH2:26][C:27]([CH3:30])([CH3:28])[CH3:29])[CH:24]=3)[N:14]=[CH:13][N:12]=2)[CH2:5][C:6]([OH:8])=[O:7])[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 117760177Ethyl 3-cyclopropyl-3-(6-((6-(2-fluoro-5-methoxyphenyl)-5-(neopentyloxy)pyridin-3-yl)methoxy)pyrimidin-4-yl)propanoate

Product 1

HCID 1177597943-Cyclopropyl-3-(6-((5-(2,2-dimethylpropoxy)-6-(2-fluoro-5-methoxyphenyl)pyridin-3-yl)methoxy)pyrimidin-4-yl)propanoic acidYield 23.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of ethyl 3-cyclopropyl-3-(6-((6-(2-fluoro-5-methoxyphenyl)-5-(neopentyloxy)pyridin-3-yl)methoxy)pyrimidin-4-yl)propanoate (20 mg) in methanol (1.0 mL) was added 2N aqueous sodium hydroxide (91 μL) solution, and the mixture was stirred at room temperature for 20 hr. The reaction mixture was cooled to 0° C. and neutralized with 1N hydrochloric acid, and extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was fractionated by HPLC (C18, mobile phase: water/acetonitrile (10 mM NH4HCO3-containing system)). The obtained fraction was evaporated under reduced pressure to give the title compound (4.4 mg) as a colorless oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customThe obtained fraction was evaporated under reduced pressure

Sources & evidence

ORD record
ord-07182ccf38e249838651bde108f54d79
Source dataset
uspto-grants-2015_11
Patent number
US09181186B2

Reaction notes

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