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

HRID 2040837Notes

Reaction equation

HRID 2040837 reaction equation
[CH2:1]([C:5]1[CH:10]=[C:9]([C:11]2[O:15][N:14]=[C:13]([C:16]3[CH:21]=[CH:20][C:19]([CH2:22][C:23](O)=[O:24])=[CH:18][CH:17]=3)[N:12]=2)[CH:8]=[C:7]([CH3:26])[N:6]=1)[CH:2]([CH3:4])[CH3:3].[CH3:27][O:28][C:29]([CH:31]1[CH2:34][NH:33][CH2:32]1)=[O:30]>[OH-].[Na+].O1CCOCC1>[CH3:27][O:28][C:29]([CH:31]1[CH2:34][N:33]([C:23](=[O:24])[CH2:22][C:19]2[CH:20]=[CH:21][C:16]([C:13]3[N:12]=[C:11]([C:9]4[CH:8]=[C:7]([CH3:26])[N:6]=[C:5]([CH2:1][CH:2]([CH3:3])[CH3:4])[CH:10]=4)[O:15][N:14]=3)=[CH:17][CH:18]=2)[CH2:32]1)=[O:30].[CH2:1]([C:5]1[CH:10]=[C:9]([C:11]2[O:15][N:14]=[C:13]([C:16]3[CH:17]=[CH:18][C:19]([CH2:22][C:23]([N:33]4[CH2:34][CH:31]([C:29]([OH:28])=[O:30])[CH2:32]4)=[O:24])=[CH:20][CH:21]=3)[N:12]=2)[CH:8]=[C:7]([CH3:26])[N:6]=1)[CH:2]([CH3:4])[CH3:3]

Participants

5

Reactant 2

HCID 20132751Methyl azetidine-3-carboxylateHCID 59234753{4-[5-(2-Isobutyl-6-methyl-pyridin-4-yl)-[1,2,4]oxadiazol-3-yl]-phenyl}-acetic acid

Product 2

HCID 592347521-(2-{4-[5-(2-Isobutyl-6-methyl-pyridin-4-yl)-[1,2,4]oxadiazol-3-yl]-phenyl}-acetyl)-azetidine-3-carboxylic acidHCID 685556431-(2-{4-[5-(2-Isobutyl-6-methyl-pyridin-4-yl)-[1,2,4]oxadiazol-3-yl]-phenyl}-acetyl)-azetidine-3-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 18323598NaOH dioxaneSolvent

Procedure

1-(2-{4-[5-(2-Isobutyl-6-methyl-pyridin-4-yl)-[1,2,4]oxadiazol-3-yl]-phenyl}-acetyl)-azetidine-3-carboxylic acid methyl ester is prepared from {4-[5-(2-isobutyl-6-methyl-pyridin-4-yl)-[1,2,4]oxadiazol-3-yl]-phenyl}-acetic acid and azetidine-3-carboxylic acid methyl ester in analogy to Example 65; stirring this material in 3 N aq. NaOH/dioxane at rt for 20 h gives 1-(2-{4-[5-(2-isobutyl-6-methyl-pyridin-4-yl)-[1,2,4]oxadiazol-3-yl]-phenyl}-acetyl)-azetidine-3-carboxylic acid; LC-MS: tR=0.80, [M+1]+=435.02.

Sources & evidence

ORD record
ord-36e69c82e9184889a8b8c7379ede49ec
Source dataset
uspto-grants-2013_11
Patent number
US08580824B2

Reaction notes

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