Oxalic Acid → 1-{2-[5-(4-Isobutylphenyl)-1,2,4-oxadiazol-3-yl]-4,5,6,7-tetrahydro-1-benzofuran-4-yl}azetidine-3-carboxylic acid

HRID 2247666Notes

Reaction equation

HRID 2247666 reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[O:15][N:14]=[C:13]([C:16]3[O:17][C:18]4[CH2:24][CH2:23][CH2:22][CH:21]([N:25]5[CH2:28][CH:27]([C:29]([O:31]CC)=[O:30])[CH2:26]5)[C:19]=4[CH:20]=3)[N:12]=2)=[CH:7][CH:6]=1)[CH:2]([CH3:4])[CH3:3].[OH-].[Na+].C(O)(=O)C(O)=O>>[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[O:15][N:14]=[C:13]([C:16]3[O:17][C:18]4[CH2:24][CH2:23][CH2:22][CH:21]([N:25]5[CH2:28][CH:27]([C:29]([OH:31])=[O:30])[CH2:26]5)[C:19]=4[CH:20]=3)[N:12]=2)=[CH:7][CH:6]=1)[CH:2]([CH3:4])[CH3:3]

Participants

4

Reactant 3

HCID 971Oxalic AcidHCID 14798Sodium HydroxideHCID 68528772HCID 68528772, compound

Product 1

HCID 592180451-{2-[5-(4-Isobutylphenyl)-1,2,4-oxadiazol-3-yl]-4,5,6,7-tetrahydro-1-benzofuran-4-yl}azetidine-3-carboxylic acidYield 55.1%

Procedure

The title compound (13 mg) was synthesized in a yield of 50% as a white crystalline solid by conducting the similar reaction to that mentioned in Example 3 (3e) using ethyl 1-{2-[5-(4-isobutylphenyl)-1,2,4-oxadiazol-3-yl]-4,5,6,7-tetrahydro-1-benzofuran-4-yl}azetidine-3-carboxylate (25 mg, 0.056 mmol) that was obtained in Example 7 (7f), a 1N aqueous solution of sodium hydroxide (0.17 ml, 0.17 mmol), and oxalic acid (3 mg, 0.028 mmol).

Workup

  1. customthe similar reaction to

Sources & evidence

ORD record
ord-ba9d1151688b4efba7ef0909c0a1d539
Source dataset
uspto-grants-2010_03
Patent number
US07687491B2

Reaction notes

Loading…