Sodium Hydroxide → sodium [3-[{(1RS,2RS)-2-(4,5-diphenyloxazol-2-yl)cyclopentan-1-yl}methyl]phenoxy]acetate

HRID 377331Notes

Reaction equation

HRID 377331 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([C:18]3[CH2:22][CH2:21][CH2:20][C:19]=3[CH2:23][C:24]3[CH:25]=[C:26]([CH:34]=[CH:35][CH:36]=3)[O:27][CH2:28][C:29]([O:31]CC)=[O:30])[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.C1(C2N=C(C3C(CC4C=C(C=CC=4)OCC(OCC)=O)CCC=3)OC=2C2C=CC=CC=2)C=CC=CC=1.C1(C2N=C(C3CCCC3CC3C=C(C=CC=3)OCC(OCC)=O)OC=2C2C=CC=CC=2)C=CC=CC=1.[OH-].[Na+:110]>C(O)C.C(OCC)(=O)C.[Pd]>[C:1]1([C:7]2[N:8]=[C:9]([CH:18]3[CH2:22][CH2:21][CH2:20][CH:19]3[CH2:23][C:24]3[CH:25]=[C:26]([CH:34]=[CH:35][CH:36]=3)[O:27][CH2:28][C:29]([O-:31])=[O:30])[O:10][C:11]=2[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1.[Na+:110]

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 54031249Ethyl [3-[[2-(4,5-diphenyloxazol-2-yl)-1-cyclopenten-1-yl]methyl]phenoxy]acetateHCID 54507446Ethyl [3-[[2-(4,5-diphenyloxazol-2-yl)-2-cyclopenten-1-yl]methyl]phenoxy]acetateHCID 86755138ethyl [3-[{(1RS,2RS)-2-(4,5-diphenyloxazol-2-yl)cyclopentan-1-yl}methyl]phenoxy]acetate2×

Product 1

HCID 70268840sodium [3-[{(1RS,2RS)-2-(4,5-diphenyloxazol-2-yl)cyclopentan-1-yl}methyl]phenoxy]acetate

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of a mixture (400 mg) of ethyl [3-[{2-(4,5-diphenyloxazol-2-yl)-1-cyclopenten-1-yl}methyl]-phenoxy]acetate and ethyl [3-[{2-(4,5-diphenyloxazol-2-yl)-2-cyclopenten-1-yl}methyl]phenoxy]acetate in a mixture of ethanol (10 ml) and ethyl acetate (10 ml) was added 10% palladium on carbon (50 mg). After being stirred for 6 hours under hydrogen atmosphere, the reaction mixture was filtered. The solvent was evaporated in vacuo to give a residue containing a mixture of ethyl [3-[{(1RS,2RS)-2-(4,5-diphenyloxazol-2-yl)cyclopentan-1-yl}methyl]phenoxy]acetate and ethyl [3-[{(1RS,2SR)-2-(4,5-diphenyloxazol-2-yl)cyclopentan-1-yl}methyl]phenoxy]acetate. The residue was dissolved in ethanol (20 ml), and 1N-sodium hydroxide solution (0.80 ml) was added. After being stirred for 8 hours, the solvent was evaporated in vacuo. The residue was triturated in ether to give a mixture (350 mg) of sodium [3-[{(1RS,2RS)-2-(4,5-diphenyloxazol-2-yl)cyclopentan-1-yl}methyl]phenoxy]acetate and sodium [3-[{(1RS,2SR)-2-(4,5-diphenyloxazol-2-yl)cyclopentan-1-yl}methyl]phenoxy]acetate.

Workup

  1. filtrationthe reaction mixture was filtered
  2. customThe solvent was evaporated in vacuo
  3. customto give a residue
  4. additioncontaining
  5. stirringAfter being stirred for 8 hours
  6. customthe solvent was evaporated in vacuo
  7. customThe residue was triturated in ether

Sources & evidence

ORD record
ord-a6c068ad15394d2d8bc7ec0231205765
Source dataset
uspto-grants-2000_02
Patent number
US06025375

Reaction notes

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