Lithium Hydroxide → cis(+/-)-2-(4-{[(4-Chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-(2,2-difluoropropoxy)piperidin-1-yl)-1,3-thiazole-5-carboxylic acid

HRID 1425189Notes

Reaction equation

HRID 1425189 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([C:9]([NH:11][C@H:12]2[CH2:17][CH2:16][N:15]([C:18]3[S:19][C:20]([C:23]([O:25]CC)=[O:24])=[CH:21][N:22]=3)[CH2:14][C@H:13]2[O:28][CH2:29][C:30]([F:33])([F:32])[CH3:31])=[O:10])[NH:5][C:6]=1[CH2:7][CH3:8].[OH-].[Li+]>CO>[Cl:1][C:2]1[N:3]=[C:4]([C:9]([NH:11][C@H:12]2[CH2:17][CH2:16][N:15]([C:18]3[S:19][C:20]([C:23]([OH:25])=[O:24])=[CH:21][N:22]=3)[CH2:14][C@H:13]2[O:28][CH2:29][C:30]([F:33])([F:32])[CH3:31])=[O:10])[NH:5][C:6]=1[CH2:7][CH3:8]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 86648660HCID 86648660, compound

Product 1

HCID 86648659cis(+/-)-2-(4-{[(4-Chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-(2,2-difluoropropoxy)piperidin-1-yl)-1,3-thiazole-5-carboxylic acidYield 77%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The same operation as in Example (91d) was performed using ethyl cis(±)-2-(4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-(2,2-difluoropropoxy)piperidin-1-yl)-1,3-thiazole-5-carboxylate obtained in Example (128f) (0.2 g, 0.8 mmol), 2 N lithium hydroxide (6 mL, 12 mmol) and methanol (5 mL), to obtain 145 mg of the title compound as a light brown solid (77%).

Sources & evidence

ORD record
ord-ed57c825a23d405fa7e02a75f37172ac
Source dataset
uspto-grants-2015_01
Patent number
US08927588B2

Reaction notes

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