HCID 21196521, compound → HCID 21196544, compound

HRID 1067138Notes

Reaction equation

HRID 1067138 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([C:18]3[CH:19]([CH2:24][C:25]4[C:26]([CH3:35])=[C:27]([CH:32]=[CH:33][CH:34]=4)[C:28]([O:30]C)=[O:29])[CH2:20][CH2:21][CH2:22][CH:23]=3)[O:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>CO.O1CCOCC1.[OH-].[Na+].Cl>[C:1]1([C:7]2[N:8]=[C:9]([C:18]3[CH:19]([CH2:24][C:25]4[C:26]([CH3:35])=[C:27]([CH:32]=[CH:33][CH:34]=4)[C:28]([OH:30])=[O:29])[CH2:20][CH2:21][CH2:22][CH:23]=3)[O:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 1

HCID 21196521HCID 21196521, compound

Product 1

HCID 21196544HCID 21196544, compoundYield 100%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 14798Sodium HydroxideSolventHCID 21966525Dioxane MethanolSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of methyl 3-{[2-(4,5-diphenyloxazol-2-yl)-2-cyclohexen-1-yl]methyl}-2-methylbenzoate (100 mg) in MeOH-1,4-dioxane (1:2, 4.5 ml) was added iN NaOH solution (1.0 ml) and the mixture was stirred at 70° C. for 1 hour. After cooling, the mixture was acidified with iN HCl and extracted with EtOAc. The organic layer was washed with water and brine, dried over magnesium sulfate, evaporated in vacuo to give 3-{[2-(4,5-diphenyloxazol-2-yl)-2-cyclohexen-1-yl]-methyl}-2-methylbenzoic acid (97.0 mg) as a solid.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-cb1eec6328454e2fb98d6bdf4809352f
Source dataset
uspto-grants-2001_06
Patent number
US06245790B1

Reaction notes

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