Lithium Hydroxide → HCID 21935682, compound

HRID 1242456Notes

Reaction equation

HRID 1242456 reaction equation
C([O:3][C:4](=[O:40])[C:5]([O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]2[C:18]([CH:36]3[CH2:38][CH2:37]3)=[N:19][C:20]([C:26]3[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:28][CH:27]=3)=[N:21][C:22]=2[CH2:23][O:24][CH3:25])=[CH:11][C:10]=1[CH3:39])([CH3:7])[CH3:6])C.[Li+].[OH-]>O1CCCC1.CCOCC>[CH:36]1([C:18]2[C:17]([CH2:16][O:15][C:12]3[CH:13]=[CH:14][C:9]([O:8][C:5]([CH3:6])([CH3:7])[C:4]([OH:40])=[O:3])=[C:10]([CH3:39])[CH:11]=3)=[C:22]([CH2:23][O:24][CH3:25])[N:21]=[C:20]([C:26]3[CH:31]=[CH:30][C:29]([C:32]([F:34])([F:35])[F:33])=[CH:28][CH:27]=3)[N:19]=2)[CH2:38][CH2:37]1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 67072251HCID 67072251, compound

Product 1

HCID 21935682HCID 21935682, compoundYield 80.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 215 mg (0.385 mmol) 2-{4-[4-cyclopropyl-6-methoxymethyl-2-(4-trifluoromethyl-phenyl)-pyrimidin-5-ylmethoxy]-2-methyl-phenoxy}-2-methyl-propionic acid ethyl ester and 1.1 ml 1N LiOH-solution in 2.5 ml tetrahydrofurane was stirred for 2 h at RT. The reaction mixture was taken up in ether and washed with 1N HCl and water. The crude residue was suspended in AcOEt/heptane 1:19. The resulting amorphous crystals were filtered off to provide 164 mg of pure 2-{4-[4-cyclopropyl-6-methoxymethyl-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 amorphous crystals were filtered off

Sources & evidence

ORD record
ord-63e052155b394cb285a59a14c0e5defc
Source dataset
uspto-grants-2006_10
Patent number
US07115611B2

Reaction notes

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