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

HRID 1424978Notes

Reaction equation

[CH2:1]([C:3]1[NH:7][C:6]([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])=[N:5][C:4]=1[I:30])[CH3:2].[OH-].[Li+]>>[CH2:1]([C:3]1[NH:7][C:6]([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])=[N:5][C:4]=1[I:30])[CH3:2]

Participants

Reactant 2

HCID 3939Lithium Hydroxide

HCID 86648516ethyl cis(+/-)-2-(4-{[(5-ethyl-4-iodo-1H-imidazol-2-yl)carbonyl]amino}-3-methoxypiperidin-1-yl)-4-methyl-1,3-thiazole-5-carboxylate

Product 1

HCID 86648515cis(+/-)-2-(4-{[(5-Ethyl-4-iodo-1H-imidazol-2-yl)carbonyl]amino}-3-methoxypiperidin-1-yl)-4-methyl-1,3-thiazole-5-carboxylic acidYield 32.7%

Procedure

The same operation as in Example (1i) was performed using ethyl cis(±)-2-(4-{[(5-ethyl-4-iodo-1H-imidazol-2-yl)carbonyl]amino}-3-methoxypiperidin-1-yl)-4-methyl-1,3-thiazole-5-carboxylate obtained in Example (58d) (130 mg, 0.24 mmol) and 2 N lithium hydroxide (3 mL), to obtain 40.7 mg of the title compound as a pale red solid (32%).

Sources & evidence

ORD record: ord-4e5746fb8b1d4a84b295d6de492c0bd8
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08927588B2

Reaction notes

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