Lithium Hydroxide → (2-Methyl-4-{methyl-[5-(4-trifluoromethyl-phenyl)-pyrazin-2-ylmethyl]-amino}-phenoxy)-acetic acid

HRID 1242333Notes

Reaction equation

HRID 1242333 reaction equation
C[O:2][C:3](=[O:32])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([N:12]([CH3:30])[CH2:13][C:14]2[CH:19]=[N:18][C:17]([C:20]3[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=3)=[CH:16][N:15]=2)=[CH:8][C:7]=1[CH3:31].[Li+].[OH-]>C1COCC1.C(O)C>[CH3:31][C:7]1[CH:8]=[C:9]([N:12]([CH3:30])[CH2:13][C:14]2[CH:19]=[N:18][C:17]([C:20]3[CH:21]=[CH:22][C:23]([C:26]([F:28])([F:27])[F:29])=[CH:24][CH:25]=3)=[CH:16][N:15]=2)[CH:10]=[CH:11][C:6]=1[O:5][CH2:4][C:3]([OH:32])=[O:2]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 67072215(2-Methyl-4-{methyl-[5-(4-trifluoromethyl-phenyl)-pyrazin-2-ylmethyl]-amino}-phenoxy)-acetic acid methyl ester

Product 1

HCID 21935726(2-Methyl-4-{methyl-[5-(4-trifluoromethyl-phenyl)-pyrazin-2-ylmethyl]-amino}-phenoxy)-acetic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 110 mg (0.25 mmol) (2-methyl-4-{methyl-[5-(4-trifluoromethyl-phenyl)-pyrazin-2-ylmethyl]-amino}-phenoxy)-acetic acid methyl ester in 0.75 ml of THF and 0.75 ml ethanol was treated at 0° C. with 0.74 ml 1N LiOH and stirred for 45 min at RT. The reaction was extracted with with aqueous 10% KHSO4/Et2O (3×). The organic phase was washed with aqueous 10% NaCl, dried over Na2SO4 and evaporated. The product was crystallized from ether to give pure (2-methyl-4-{methyl-[5-(4-trifluoromethyl-phenyl)-pyrazin-2-ylmethyl]-amino}-phenoxy)-acetic acid.

Workup

  1. extractionThe reaction was extracted with with aqueous 10% KHSO4/Et2O (3×)
  2. washThe organic phase was washed with aqueous 10% NaCl
  3. dry with materialdried over Na2SO4
  4. customevaporated
  5. customThe product was crystallized from ether

Sources & evidence

ORD record
ord-4e711e9c2dfe4552b9151d542f8f6911
Source dataset
uspto-grants-2006_10
Patent number
US07115611B2

Reaction notes

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