Sodium Hydroxide → (2-(3-Methoxy-propyl)-4-{methyl-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethyl]-amino}-phenoxy)-acetic acid

HRID 1393100Notes

Reaction equation

HRID 1393100 reaction equation
C([O:3][C:4](=[O:37])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]([CH3:31])[CH2:14][C:15]2[S:19][C:18]([C:20]3[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=3)=[N:17][C:16]=2[CH3:30])=[CH:9][C:8]=1[CH2:32][CH2:33][CH2:34][O:35][CH3:36])C.[OH-].[Na+]>C1COCC1.CCO>[CH3:36][O:35][CH2:34][CH2:33][CH2:32][C:8]1[CH:9]=[C:10]([N:13]([CH3:31])[CH2:14][C:15]2[S:19][C:18]([C:20]3[CH:21]=[CH:22][C:23]([C:26]([F:28])([F:29])[F:27])=[CH:24][CH:25]=3)=[N:17][C:16]=2[CH3:30])[CH:11]=[CH:12][C:7]=1[O:6][CH2:5][C:4]([OH:37])=[O:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69220724(2-(3-Methoxy-propyl)-4-{methyl-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethyl]-amino}-phenoxy)-acetic acid ethyl ester

Product 1

HCID 11477701(2-(3-Methoxy-propyl)-4-{methyl-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethyl]-amino}-phenoxy)-acetic acid

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

0.280 g (0.52 mmol) of the above prepared (2-(3-methoxy-propyl)-4-{methyl-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethyl]-amino}-phenoxy)-acetic acid ethyl ester was dissolved in 3.3 ml of THF/EtOH=1/1, treated with 1.56 ml (3 eq.) of 1N NaOH, and kept at ambient temperature for 0.5 h. The reaction mixture was then poured onto crashed ice/HCl dil., extracted twice with EtOAc, the organic layer washed with water and brine, dried over sodium sulfate, and evaporated to dryness. Crystallization from hexane/EtOAc afforded finally 0.209 g of the title compound as off-white crystals of mp. 142-143° C., MS: 507.5 (M-H)−.

Workup

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

Sources & evidence

ORD record
ord-faefa4b1870a4f169d3fc246c4e39ba6
Source dataset
uspto-grants-2008_03
Patent number
US07345067B2

Reaction notes

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