Sodium Hydroxide → HCID 11260114, compound

HRID 1393103Notes

Reaction equation

HRID 1393103 reaction equation
C([O:3][C:4](=[O:35])[CH2:5][O:6][C:7]1[C:12]([CH3:13])=[CH:11][C:10]([N:14]([CH2:32][CH3:33])[CH2:15][C:16]2[S:20][C:19]([C:21]3[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=3)=[N:18][C:17]=2[CH3:31])=[CH:9][C:8]=1[CH3:34])C.[OH-].[Na+]>C1COCC1.CCO>[CH2:32]([N:14]([CH2:15][C:16]1[S:20][C:19]([C:21]2[CH:22]=[CH:23][C:24]([C:27]([F:28])([F:29])[F:30])=[CH:25][CH:26]=2)=[N:18][C:17]=1[CH3:31])[C:10]1[CH:11]=[C:12]([CH3:13])[C:7]([O:6][CH2:5][C:4]([OH:35])=[O:3])=[C:8]([CH3:34])[CH:9]=1)[CH3:33]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69220617HCID 69220617, compound

Product 1

HCID 11260114HCID 11260114, compound

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

0.66 g (0.13 mmol) of the above prepared (4-{ethyl-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethyl]-amino}-2,6-dimethyl-phenoxy)-acetic acid ethyl ester was dissolved in 0.80 ml of THF/EtOH=1/1, treated with 0.40 ml (3 eq.) of 1N NaOH, and kept at ambient temperature for 1 h. The reaction mixture was then poured onto crashed ice/EtOAc/HCl dil., the organic layer was washed with water and brine, dried over sodium sulfate, and evaporated to dryness. Crystallization from hexane/EtOAc generated finally 0.056 g of the title compound as off-white crystals of mp. 161-162° C., MS: 477.0 (M-H)−.

Workup

  1. additionThe reaction mixture was then poured
  2. washthe organic layer was washed with water and brine
  3. dry with materialdried over sodium sulfate
  4. customevaporated to dryness
  5. customCrystallization from hexane/EtOAc

Sources & evidence

ORD record
ord-fa38c68253c547b2bacd20a91d42062a
Source dataset
uspto-grants-2008_03
Patent number
US07345067B2

Reaction notes

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