Ethyl Acetate → 3-{4-[2-(2-Cyclohexyl-5-methyl-oxazol-4-yl)-ethoxy]-3,5-dimethyl-phenyl}-2-isopropoxy-propionic acid

HRID 2215211Notes

Reaction equation

HRID 2215211 reaction equation
C([O:3][C:4](=[O:34])[CH:5]([O:30][CH:31]([CH3:33])[CH3:32])[CH2:6][C:7]1[CH:12]=[C:11]([CH3:13])[C:10]([O:14][CH2:15][CH2:16][C:17]2[N:18]=[C:19]([CH:23]3[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]3)[O:20][C:21]=2[CH3:22])=[C:9]([CH3:29])[CH:8]=1)C.[OH-].[Na+].CCOC(C)=O>C1COCC1.CCO>[CH:23]1([C:19]2[O:20][C:21]([CH3:22])=[C:17]([CH2:16][CH2:15][O:14][C:10]3[C:9]([CH3:29])=[CH:8][C:7]([CH2:6][CH:5]([O:30][CH:31]([CH3:32])[CH3:33])[C:4]([OH:34])=[O:3])=[CH:12][C:11]=3[CH3:13])[N:18]=2)[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 694868163-{4-[2-(2-Cyclohexyl-5-methyl-oxazol-4-yl)-ethoxy]-3,5-dimethyl-phenyl}-2-isopropoxy-propionic acid ethyl ester

Product 1

HCID 219496383-{4-[2-(2-Cyclohexyl-5-methyl-oxazol-4-yl)-ethoxy]-3,5-dimethyl-phenyl}-2-isopropoxy-propionic acidYield 87.5%

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

0.181 g of the above prepared 3-{4-[2-(2-cyclohexyl-5-methyl-oxazol-4-yl)-ethoxy]-3,5-dimethyl-phenyl}-2-isopropoxy-propionic acid ethyl ester (0.384 mmol) was dissolved in 6 ml of THF/EtOH=1/1, treated with 0.959 ml of 2N NaOH (5 eq.), and kept at ambient temperature for 14 h. The reaction mixture was then poured onto crashed ice/AcOEt/HCl dil., the aqueous phase reextracted once more with AcOEt, the combined organic layers washed with water, dried over magnesium sulfate, and evaporated to dryness. Boiling up in hexane, followed by decantation after cooling, yielded 0.149 g of the title compound as pale-yellow oil.

Workup

  1. additionThe reaction mixture was then poured
  2. washthe combined organic layers washed with water
  3. dry with materialdried over magnesium sulfate
  4. customevaporated to dryness
  5. temperatureafter cooling

Sources & evidence

ORD record
ord-2236c16a700d4fa28a8e9e30544a3dc0
Source dataset
uspto-grants-2006_09
Patent number
US07109225B2

Reaction notes

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