Water → cis(+/-)-2-(4-{[(4-Chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-isopropoxypiperidin-1-yl)-4-(2-methoxyethylcarbamoyl)-1,3-thiazole-5-carboxylic acid

HRID 1425218Notes

Reaction equation

HRID 1425218 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:30]([O:32]CC)=[O:31])=[C:21]([C:23](=[O:29])[NH:24][CH2:25][CH2:26][O:27][CH3:28])[N:22]=3)[CH2:14][C@H:13]2[O:35][CH:36]([CH3:38])[CH3:37])=[O:10])[NH:5][C:6]=1[CH2:7][CH3:8].O.[OH-].[Li+].O>O1CCCC1>[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:30]([OH:32])=[O:31])=[C:21]([C:23](=[O:29])[NH:24][CH2:25][CH2:26][O:27][CH3:28])[N:22]=3)[CH2:14][C@H:13]2[O:35][CH:36]([CH3:37])[CH3:38])=[O:10])[NH:5][C:6]=1[CH2:7][CH3:8]

Participants

5

Reactant 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 86648690Ethyl cis(+/-)-2-(4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-isopropoxypiperidin-1-yl)-4-(2-methoxyethylcarbamoyl)-1,3-thiazole-5-carboxylate

Product 1

HCID 86648691cis(+/-)-2-(4-{[(4-Chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-isopropoxypiperidin-1-yl)-4-(2-methoxyethylcarbamoyl)-1,3-thiazole-5-carboxylic acidYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl cis(±)-2-(4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-isopropoxypiperidin-1-yl)-4-(2-methoxyethylcarbamoyl)-1,3-thiazole-5-carboxylate obtained in Example (149b) (0.180 g, 0.315 mmol) was dissolved in tetrahydrofuran (5 mL). The solution was subjected to the same operation as in Example (1i) using lithium hydroxide monohydrate (52.9 g, 1.26 mmol) and water (5 mL), to obtain 0.167 g of the title compound as a white solid (98%).

Sources & evidence

ORD record
ord-2d0c8b46d4454847a736dec018bf9c1b
Source dataset
uspto-grants-2015_01
Patent number
US08927588B2

Reaction notes

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