Methyl azetidine-3-carboxylate → 1-(2-{4-[5-(6-Isobutyl-5-methyl-pyridin-3-yl)-[1,2,4]oxadiazol-3-yl]-phenyl}-acetyl)-azetidine-3-carboxylic acid

HRID 2065922Notes

Reaction equation

HRID 2065922 reaction equation
[CH2:1]([C:5]1[N:10]=[CH:9][C:8]([C:11]2[O:15][N:14]=[C:13]([C:16]3[CH:21]=[CH:20][C:19]([CH2:22][C:23]([OH:25])=O)=[CH:18][CH:17]=3)[N:12]=2)=[CH:7][C:6]=1[CH3:26])[CH:2]([CH3:4])[CH3:3].C[O:28][C:29]([CH:31]1[CH2:34][NH:33][CH2:32]1)=[O:30]>[OH-].[Na+].O1CCOCC1>[CH2:1]([C:5]1[N:10]=[CH:9][C:8]([C:11]2[O:15][N:14]=[C:13]([C:16]3[CH:21]=[CH:20][C:19]([CH2:22][C:23]([N:33]4[CH2:34][CH:31]([C:29]([OH:30])=[O:28])[CH2:32]4)=[O:25])=[CH:18][CH:17]=3)[N:12]=2)=[CH:7][C:6]=1[CH3:26])[CH:2]([CH3:4])[CH3:3]

Participants

4

Reactant 2

HCID 20132751Methyl azetidine-3-carboxylateHCID 59392514{4-[5-(6-Isobutyl-5-methyl-pyridin-3-yl)-[1,2,4]oxadiazol-3-yl]-phenyl}-acetic acid

Product 1

HCID 593925081-(2-{4-[5-(6-Isobutyl-5-methyl-pyridin-3-yl)-[1,2,4]oxadiazol-3-yl]-phenyl}-acetyl)-azetidine-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 18323598NaOH dioxaneSolvent

Procedure

1-(2-{4-[5-(6-Isobutyl-5-methyl-pyridin-3-yl)-[1,2,4]oxadiazol-3-yl]-phenyl}-acetyl)-azetidine-3-carboxylic acid is prepared from {4-[5-(6-Isobutyl-5-methyl-pyridin-3-yl)-[1,2,4]oxadiazol-3-yl]-phenyl}-acetic acid and azetidine-3-carboxylic acid methyl ester in analogy to Example 55; stirring this material in 3 N aq. NaOH/dioxane at rt for 20 h gives the desired compound; LC-MS: tR=0.60, [M+1]+=434.96.

Sources & evidence

ORD record
ord-83e44cf885c34a3198e03505c1cdfaed
Source dataset
uspto-grants-2012_10
Patent number
US08288554B2

Reaction notes

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