Lithium Hydroxide → HCID 21935807, compound

HRID 1242435Notes

Reaction equation

HRID 1242435 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][O:35][CH3:36])=[N:19][C:20]([C:23]3[CH:24]=[N:25][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:27][CH:28]=3)=[N:21][CH:22]=2)=[CH:11][C:10]=1[CH3:37])([CH3:7])[CH3:6])C.[Li+].[OH-]>C1COCC1.CO.CCOCC>[CH3:36][O:35][CH2:34][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:24]=[N:25][C:26]([C:29]([F:32])([F:30])[F:31])=[CH:27][CH:28]=2)[N:19]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 67072194HCID 67072194, compound

Product 1

HCID 21935807HCID 21935807, compoundYield 52.2%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A solution of 133 mg (0.25 mmol) 2-{4-[4-(2-methoxy-ethyl)-2-(6-trifluoromethyl-pyridin-3-yl)-pyrimidin-5-ylmethoxy]-2-methyl-phenoxy}-2-methyl-propionic acid ethyl ester (example 101A]) in 1.5 ml of THF/MeOH (1:1) was cooled (0° C.) treated with 0.75 ml 1N LiOH and stirred for 15 h at RT. The reaction mixture was taken up in ether and washed with aqueous 10% KHSO4 solution and aqueous 10% NaCl. The organic phase was dried (Na2SO4) and evaporated. The crude product was suspended in ether (RT to 4° C.) and filtered to give 66 mg of the title compound as a white powder of mp. 140.5–141.5° C., dec.

Workup

  1. washwashed with aqueous 10% KHSO4 solution and aqueous 10% NaCl
  2. dry with materialThe organic phase was dried (Na2SO4)
  3. customevaporated
  4. customwas suspended in ether (RT to 4° C.)
  5. filtrationfiltered

Sources & evidence

ORD record
ord-1fdb5d55f5d94660a9e00bd9f443f5d6
Source dataset
uspto-grants-2006_10
Patent number
US07115611B2

Reaction notes

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