Lithium Hydroxide → HCID 11432974, compound

HRID 1393115Notes

Reaction equation

HRID 1393115 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[S:18][C:17]([C:19]3[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=3)=[N:16][C:15]=2[CH3:29])=[CH:8][C:7]=1[I:31].[Li+].[OH-]>C1COCC1.C(O)C>[I:31][C:7]1[CH:8]=[C:9]([N:12]([CH3:30])[CH2:13][C:14]2[S:18][C:17]([C:19]3[CH:24]=[CH:23][C:22]([C:25]([F:26])([F:27])[F:28])=[CH:21][CH:20]=3)=[N:16][C:15]=2[CH3:29])[CH:10]=[CH:11][C:6]=1[O:5][CH2:4][C:3]([OH:32])=[O:2]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 69217922HCID 69217922, compound

Product 1

HCID 11432974HCID 11432974, compoundYield 58.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of (2-iodo-4-{methyl-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethyl]-amino}-phenoxy)-acetic acid methyl ester (140 mg, 0.24 mmol) in THF (1.2 ml) and ethanol (1.2 ml) was treated at 0° C. with 1N LiOH (0.73 ml) and stirred for 3 h at RT. The reaction was extracted 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 CH2Cl2 to give 79 mg of pure (2-iodo-4-{methyl-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethyl]-amino}-phenoxy)-acetic acid, MS: 561.1 (M-H)−, MP: 172.5-173.0° C.

Workup

  1. extractionThe reaction was extracted 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 CH2Cl2

Sources & evidence

ORD record
ord-5693a95d3415471f87a2394463dd58f7
Source dataset
uspto-grants-2008_03
Patent number
US07345067B2

Reaction notes

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