Lithium Hydroxide → cis(+/-)-2-(4-{[(4-Bromo-5-methyl-1H-imidazol-2-yl)carbonyl]amino}-3-methoxypiperidin-1-yl)-4-methyl-1,3-thiazole-5-carboxylic acid

HRID 43457Notes

Reaction equation

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

Participants

Reactant 2

HCID 3939Lithium Hydroxide

HCID 86648476ethyl cis(+/-)-2-(4-{[(4-bromo-5-methyl-1H-imidazol-2-yl)carbonyl]amino}-3-methoxypiperidin-1-yl)-4-methyl-1,3-thiazole-5-carboxylate

Product 1

HCID 86648475cis(+/-)-2-(4-{[(4-Bromo-5-methyl-1H-imidazol-2-yl)carbonyl]amino}-3-methoxypiperidin-1-yl)-4-methyl-1,3-thiazole-5-carboxylic acidYield 61.5%

Procedure

The same operation as in Example (1i) was performed using ethyl cis(±)-2-(4-{[(4-bromo-5-methyl-1H-imidazol-2-yl)carbonyl]amino}-3-methoxypiperidin-1-yl)-4-methyl-1,3-thiazole-5-carboxylate obtained in Example (31d) (0.19 g, 0.39 mmol) and 2 N lithium hydroxide (4 mL), to obtain 0.11 g of the title compound as a white solid (61%).

Sources & evidence

ORD record: ord-e97fdaf2f87d440bbbd491b394e93b14
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08536197B2

Reaction notes

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