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

HRID 2247775Notes

Reaction equation

HRID 2247775 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[CH:17]=[CH:18][C:19]([CH2:22][N:23]4[CH2:26][CH:25]([C:27]([O:29]C)=[O:28])[CH2:24]4)=[N:20][CH:21]=3)[N:12]=2)=[CH:7][C:6]=1[CH3:31])[CH:2]([CH3:4])[CH3:3].[OH-].[Na+].C(O)(=O)C.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[CH:17]=[CH:18][C:19]([CH2:22][N:23]4[CH2:26][CH:25]([C:27]([OH:29])=[O:28])[CH2:24]4)=[N:20][CH:21]=3)[N:12]=2)=[CH:7][C:6]=1[CH3:31])[CH:2]([CH3:4])[CH3:3]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 971Oxalic AcidHCID 14798Sodium HydroxideHCID 68528706Methyl 1-({5-[5-(4-isobutyl-3-methylphenyl)-1,2,4-oxadiazol-3-yl]pyridin-2-yl}methyl)azetidine-3-carboxylate

Product 1

HCID 119782791-({5-[5-(4-Isobutyl-3-methylphenyl)-1,2,4-oxadiazol-3-yl]pyridin-2-yl}methyl)azetidine-3-carboxylic acidYield 94.1%

Procedure

The title compound (0.13 g) was synthesized in a yield of 83% as a white crystalline solid by conducting the reaction similar to that mentioned in Example 21 (21d) using methyl 1-({5-[5-(4-isobutyl-3-methylphenyl)-1,2,4-oxadiazol-3-yl]pyridin-2-yl}methyl)azetidine-3-carboxylate (0.14 g, 0.34 mmol) that was obtained in Example 28 (28b), a 1 N aqueous solution of sodium hydroxide (11.0 mL, 1.0 mmol), acetic acid (58 μL, 1.0 mmol), and oxalic acid (15 mg, 0.17 mmol).

Workup

  1. customthe reaction similar to

Sources & evidence

ORD record
ord-02d77bf39201461fb08359139d5261a8
Source dataset
uspto-grants-2010_03
Patent number
US07687491B2

Reaction notes

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