Lithium Hydroxide → HCID 11167960, compound

HRID 1242330Notes

Reaction equation

HRID 1242330 reaction equation
C([O:5][C:6](=[O:40])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH:16]([C:20]2[C:21]([CH:36]3[CH2:38][CH2:37]3)=[N:22][C:23]([C:26]3[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:28][CH:27]=3)=[N:24][CH:25]=2)[CH2:17][CH2:18][CH3:19])=[CH:11][C:10]=1[CH3:39])(C)(C)C.[OH-].[Li+]>C1COCC1>[CH:36]1([C:21]2[C:20]([CH:16]([O:15][C:12]3[CH:13]=[CH:14][C:9]([O:8][CH2:7][C:6]([OH:40])=[O:5])=[C:10]([CH3:39])[CH:11]=3)[CH2:17][CH2:18][CH3:19])=[CH:25][N:24]=[C:23]([C:26]3[CH:31]=[CH:30][C:29]([C:32]([F:34])([F:35])[F:33])=[CH:28][CH:27]=3)[N:22]=2)[CH2:38][CH2:37]1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 67072383HCID 67072383, compound

Product 1

HCID 11167960HCID 11167960, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 150 mg (0.261 mmol) [rac]-(4-{1-[4-cyclopropyl-2-(4-trifluoromethyl-phenyl)-pyrimidin-5-yl]-butoxy}-2-methyl-phenoxy)-acetic acid tert-butyl ester and 0.52 ml 1N lithium hydroxide solution in 1.5 ml THF were stirred at RT for 2 h. The solution was partitioned between ether, 1N HCl and water and the ether layer then concentrated under reduced pressure. The crude product was repeatedly concentrated in with ether until a foam of 121 mg pure [rac]-(4-{1-[4-cyclopropyl-2-(4-trifluoromethyl-phenyl)-pyrimidin-5-yl]-butoxy}-2-methyl-phenoxy)-acetic acid was obtained.

Workup

  1. customThe solution was partitioned between ether, 1N HCl and water
  2. concentrationthe ether layer then concentrated under reduced pressure
  3. concentrationThe crude product was repeatedly concentrated in with ether until a foam of 121 mg pure [rac]-(4-{1-[4-cyclopropyl-2-(4-trifluoromethyl-phenyl)-pyrimidin-5-yl]-butoxy}-2-methyl-phenoxy)-acetic acid
  4. customwas obtained

Sources & evidence

ORD record
ord-3149301bb88c4123ac2111c943209ec3
Source dataset
uspto-grants-2006_10
Patent number
US07115611B2

Reaction notes

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