Acetic Acid → 1-({5-[5-(4-Isobutyl-3-methylphenyl)-1,2,4-oxadiazol-3-yl]-6-methylpyridin-2-yl}methyl)azetidine-3-carboxylic acid

HRID 2247772Notes

Reaction equation

HRID 2247772 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]([CH2:23][N:24]4[CH2:27][CH:26]([C:28]([O:30]C)=[O:29])[CH2:25]4)=[N:20][C:21]=3[CH3:22])[N:12]=2)=[CH:7][C:6]=1[CH3:32])[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]([CH2:23][N:24]4[CH2:27][CH:26]([C:28]([OH:30])=[O:29])[CH2:25]4)=[N:20][C:21]=3[CH3:22])[N:12]=2)=[CH:7][C:6]=1[CH3:32])[CH:2]([CH3:4])[CH3:3]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 971Oxalic AcidHCID 14798Sodium HydroxideHCID 68525220Methyl 1-({5-[5-(4-isobutyl-3-methylphenyl)-1,2,4-oxadiazol-3-yl]-6-methylpyridin-2-yl}methyl)azetidine-3-carboxylate

Product 1

HCID 119782821-({5-[5-(4-Isobutyl-3-methylphenyl)-1,2,4-oxadiazol-3-yl]-6-methylpyridin-2-yl}methyl)azetidine-3-carboxylic acidYield 84.9%

Procedure

The title compound (0.10 g) was synthesized in a yield of 78% as a white crystalline solid by conducting the similar reaction to that mentioned in Example 21 (21d) using methyl 1-({5-[5-(4-isobutyl-3-methylphenyl)-1,2,4-oxadiazol-3-yl]-6-methylpyridin-2-yl}methyl)azetidine-3-carboxylate (0.12 g, 0.28 mmol) that was obtained in Example 27 (27f), a 1N aqueous solution of sodium hydroxide (0.84 ml, 0.84 mmol), acetic acid (48 μl, 0.84 mmol), and oxalic acid (13 mg, 0.14 mmol).

Workup

  1. customthe similar reaction to

Sources & evidence

ORD record
ord-f34240b307e7421e8046a3e92871c7bc
Source dataset
uspto-grants-2010_03
Patent number
US07687491B2

Reaction notes

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