Lithium Hydroxide → [Rac]-(4-{1-[4-cyclopropyl-2-(4-trifluoromethyl-phenyl)-pyrimidin-5-yl]-ethoxy}-2-methyl-phenoxy)-acetic acid

HRID 1242327Notes

Reaction equation

HRID 1242327 reaction equation
C([O:3][C:4](=[O:36])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH:14]([C:16]2[C:17]([CH:32]3[CH2:34][CH2:33]3)=[N:18][C:19]([C:22]3[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=3)=[N:20][CH:21]=2)[CH3:15])=[CH:9][C:8]=1[CH3:35])C.[Li+].[OH-]>C1COCC1.CCOCC>[CH:32]1([C:17]2[C:16]([CH:14]([O:13][C:10]3[CH:11]=[CH:12][C:7]([O:6][CH2:5][C:4]([OH:36])=[O:3])=[C:8]([CH3:35])[CH:9]=3)[CH3:15])=[CH:21][N:20]=[C:19]([C:22]3[CH:23]=[CH:24][C:25]([C:28]([F:30])([F:31])[F:29])=[CH:26][CH:27]=3)[N:18]=2)[CH2:33][CH2:34]1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 67072201[Rac]-(4-{1-[4-cyclopropyl-2-(4-trifluoromethyl-phenyl)-pyrimidin-5-yl]-ethoxy}-2-methyl-phenoxy)-acetic acid ethyl ester

Product 1

HCID 11155681[Rac]-(4-{1-[4-cyclopropyl-2-(4-trifluoromethyl-phenyl)-pyrimidin-5-yl]-ethoxy}-2-methyl-phenoxy)-acetic acidYield 86.2%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

154 mg (0.307 mmol) of [rac]-(4-{1-[4-cyclopropyl-2-(4-trifluoromethyl-phenyl)-pyrimidin-5-yl]-ethoxy}-2-methyl-phenoxy)-acetic acid ethyl ester and 0.62 ml 1N LiOH in 1.6 ml THF were stirred for 2 h at RT. The reaction mixture was taken up in ether and washed with 1N HCl and water. The crude product was suspended in AcOEt/heptane 1:19 and the resulting crystals were filtered off to give 125 mg of pure [rac]-(4-{1-[4-cyclopropyl-2-(4-trifluoromethyl-phenyl)-pyrimidin-5-yl]-ethoxy}-2-methyl-phenoxy)-acetic acid.

Workup

  1. washwashed with 1N HCl and water
  2. filtrationthe resulting crystals were filtered off

Sources & evidence

ORD record
ord-9fdeaf6c301d43c9986d71d64d025c66
Source dataset
uspto-grants-2006_10
Patent number
US07115611B2

Reaction notes

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