Hydrochloric Acid → [Rac]-3-{4-[2-(4-tert-butyl-phenyl)-thiazol-4-ylmethoxy]-3-methyl-phenyl}-2-ethoxy-propionic acid

HRID 394229Notes

Reaction equation

HRID 394229 reaction equation
C([O:3][C:4](=[O:34])[CH:5]([O:31][CH2:32][CH3:33])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][C:15]2[N:16]=[C:17]([C:20]3[CH:25]=[CH:24][C:23]([C:26]([CH3:29])([CH3:28])[CH3:27])=[CH:22][CH:21]=3)[S:18][CH:19]=2)=[C:9]([CH3:30])[CH:8]=1)C.[OH-].[Li+].Cl.S([O-])(O)(=O)=O.[K+]>CO>[C:26]([C:23]1[CH:22]=[CH:21][C:20]([C:17]2[S:18][CH:19]=[C:15]([CH2:14][O:13][C:10]3[CH:11]=[CH:12][C:7]([CH2:6][CH:5]([O:31][CH2:32][CH3:33])[C:4]([OH:34])=[O:3])=[CH:8][C:9]=3[CH3:30])[N:16]=2)=[CH:25][CH:24]=1)([CH3:29])([CH3:28])[CH3:27]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 516920Potassium bisulfateHCID 68616333[Rac]-3-{4-[2-(4-tert-butyl-phenyl)-thiazol-4-ylmethoxy]-3-methyl-phenyl}-2-ethoxy-propionic acid ethyl ester

Product 1

HCID 22647524[Rac]-3-{4-[2-(4-tert-butyl-phenyl)-thiazol-4-ylmethoxy]-3-methyl-phenyl}-2-ethoxy-propionic acidYield 98.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
55 °C

Procedure

140 mg of [rac]-3-{4-[2-(4-tert-butyl-phenyl)-thiazol-4-ylmethoxy]-3-methyl-phenyl}-2-ethoxy-propionic acid ethyl ester (0.29 mmol) were dissolved in 5 ml of methanol; 1 ml of a 2N aqueous lithium hydroxide solution was added and the reaction mixture was stirred at 55° C. for 1 h. After cooling to room temperature, 1 ml of a 2N aqueous hydrochloric acid solution and 0.5 ml of a saturated solution of potassium hydrogen sulfate were added. The reaction mixture was then extracted with two 10 ml portions of dichloromethane. The combined organic phases were washed with brine, dried over anhydrous sodium sulfate and evaporated, leaving 130 mg (98.6% of theory) of [rac]-3-{4-[2-(4-tert-butyl-phenyl)-thiazol-4-ylmethoxy]-3-methyl-phenyl}-2-ethoxy-propionic acid as a colorless solid.

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionThe reaction mixture was then extracted with two 10 ml portions of dichloromethane
  3. washThe combined organic phases were washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-e816329aef26495b8872f233717c21e8
Source dataset
uspto-grants-2004_10
Patent number
US06809110B2

Reaction notes

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