Lithium Hydroxide → HCID 21935681, compound

HRID 1242462Notes

Reaction equation

HRID 1242462 reaction equation
C([O:3][C:4](=[O:38])[C:5]([O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]2[C:18]([CH2:33][CH2:34][CH2:35][CH3:36])=[N:19][C:20]([C:23]3[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=3)=[N:21][CH:22]=2)=[CH:11][C:10]=1[CH3:37])([CH3:7])[CH3:6])C.[Li+].[OH-]>O1CCCC1.CCOCC>[CH2:33]([C:18]1[C:17]([CH2:16][O:15][C:12]2[CH:13]=[CH:14][C:9]([O:8][C:5]([CH3:6])([CH3:7])[C:4]([OH:38])=[O:3])=[C:10]([CH3:37])[CH:11]=2)=[CH:22][N:21]=[C:20]([C:23]2[CH:28]=[CH:27][C:26]([C:29]([F:31])([F:32])[F:30])=[CH:25][CH:24]=2)[N:19]=1)[CH2:34][CH2:35][CH3:36]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 67072271HCID 67072271, compound

Product 1

HCID 21935681HCID 21935681, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

324 mg (0.61 mmol) of 2-{4-[4-butyl-2-(4-trifluoromethyl-phenyl)-pyrimidin-5-ylmethoxy]-2-methyl-phenoxy}-2-methyl-propionic acid ethyl ester and 1.83 ml 1N LiOH in 3 ml terahydrofurane were stirred over night 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. The resulting crystals were filtered off providing 282 mg pure 2-{4-[4-butyl-2-(4-trifluoromethyl-phenyl)-pyrimidin-5-ylmethoxy]-2-methyl-phenoxy}-2-methyl-propionic acid.

Workup

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

Sources & evidence

ORD record
ord-155b1bd5ca3b43f3ae7638cfeb124ff3
Source dataset
uspto-grants-2006_10
Patent number
US07115611B2

Reaction notes

Loading…