Methanol → cis(+/-)-2-(3-Butoxy-4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}piperidin-1-yl)-4-methyl-1,3-thiazole-5-carboxylic acid

HRID 43687Notes

Reaction equation

HRID 43687 reaction equation
[CH2:1]([O:5][C@H:6]1[C@@H:11]([NH:12][C:13]([C:15]2[NH:16][C:17]([CH2:21][CH3:22])=[C:18]([Cl:20])[N:19]=2)=[O:14])[CH2:10][CH2:9][N:8]([C:23]2[S:24][C:25]([C:29]([O:31]CC)=[O:30])=[C:26]([CH3:28])[N:27]=2)[CH2:7]1)[CH2:2][CH2:3][CH3:4].[OH-].[Li+].CO>C1COCC1>[CH2:1]([O:5][C@H:6]1[C@@H:11]([NH:12][C:13]([C:15]2[NH:16][C:17]([CH2:21][CH3:22])=[C:18]([Cl:20])[N:19]=2)=[O:14])[CH2:10][CH2:9][N:8]([C:23]2[S:24][C:25]([C:29]([OH:31])=[O:30])=[C:26]([CH3:28])[N:27]=2)[CH2:7]1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 86648629ethyl cis(+/-)-2-(3-butoxy-4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}piperidin-1-yl)-4-methyl-1,3-thiazole-5-carboxylate

Product 1

HCID 86648628cis(+/-)-2-(3-Butoxy-4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}piperidin-1-yl)-4-methyl-1,3-thiazole-5-carboxylic acidYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The same operation as in Example (91d) was performed using ethyl cis(±)-2-(3-butoxy-4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}piperidin-1-yl)-4-methyl-1,3-thiazole-5-carboxylate obtained in Example (120a) (0.34 g, 0.68 mmol), 2 N lithium hydroxide (5 mL, 10 mmol), methanol (3 mL) and THF (5 mL), to obtain 0.28 g of the title compound as a colorless solid (88%).

Sources & evidence

ORD record
ord-dfdebec6e3b84dad858a253707ec09f0
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

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