Acetic Acid → 1-({5-[5-(4-Cyclohexylphenyl)-1,2,4-oxadiazol-3-yl]-2-furyl}methyl)azetidine-3-carboxylic acid

HRID 2247643Notes

Reaction equation

HRID 2247643 reaction equation
[CH:1]1([C:7]2[CH:12]=[CH:11][C:10]([C:13]3[O:17][N:16]=[C:15]([C:18]4[O:22][C:21]([CH2:23][N:24]5[CH2:27][CH:26]([C:28]([O:30]CC)=[O:29])[CH2:25]5)=[CH:20][CH:19]=4)[N:14]=3)=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.O1CCCC1.O.[OH-].[Li+].C(O)(=O)C>O.CO>[CH:1]1([C:7]2[CH:8]=[CH:9][C:10]([C:13]3[O:17][N:16]=[C:15]([C:18]4[O:22][C:21]([CH2:23][N:24]5[CH2:27][CH:26]([C:28]([OH:30])=[O:29])[CH2:25]5)=[CH:20][CH:19]=4)[N:14]=3)=[CH:11][CH:12]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 68524364HCID 68524364, compound

Product 1

HCID 119778161-({5-[5-(4-Cyclohexylphenyl)-1,2,4-oxadiazol-3-yl]-2-furyl}methyl)azetidine-3-carboxylic acidYield 56.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of ethyl 1-({5-[5-(4-cyclohexylphenyl)-1,2,4-oxadiazol-3-yl]-2-furyl}methyl)azetidine-3-carboxylate (0.23 g, 0.53 mmol) that was obtained in Example 2 (2d) in a mixed solvent of tetrahydrofuran (0.50 ml), methanol (0.50 ml) and water (0.50 ml) was added lithium hydroxide monohydrate (50 mg, 1.2 mmol) with stirring, and the resulting mixture was stirred at room temperature for 1 hour. After stirring, acetic acid (65 μl, 1.2 mmol) was added to the reaction mixture to quench the reaction. The white solid precipitated was collected by filtration using a Kiriyama funnel, washed with a mixed solvent of water and methanol (3:7) and dried in vacuo to afford the title compound (122 mg) in a yield of 56% as a white crystalline solid.

Workup

  1. stirringthe resulting mixture was stirred at room temperature for 1 hour
  2. stirringAfter stirring
  3. customto quench
  4. customthe reaction
  5. customThe white solid precipitated
  6. filtrationwas collected by filtration
  7. washwashed with a mixed solvent of water and methanol (3:7)
  8. customdried in vacuo

Sources & evidence

ORD record
ord-79546d31bb11429d8d3129d7ea71e82d
Source dataset
uspto-grants-2010_03
Patent number
US07687491B2

Reaction notes

Loading…