Lithium Hydroxide → trans(+/-)-2-[(5-{[(4-Chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-1,3-dihydro-2H-isoindol-2-yl) carbonyl]cyclopropanecarboxylic acid

HRID 1425039Notes

Reaction equation

HRID 1425039 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([C:9]([NH:11][C:12]2[CH:13]=[C:14]3[C:18](=[CH:19][CH:20]=2)[CH2:17][N:16]([C:21]([C@@H:23]2[CH2:25][C@H:24]2[C:26]([O:28]CC)=[O:27])=[O:22])[CH2:15]3)=[O:10])[NH:5][C:6]=1[CH2:7][CH3:8].[OH-].[Li+]>CO.ClCCl>[Cl:1][C:2]1[N:3]=[C:4]([C:9]([NH:11][C:12]2[CH:13]=[C:14]3[C:18](=[CH:19][CH:20]=2)[CH2:17][N:16]([C:21]([C@@H:23]2[CH2:25][C@H:24]2[C:26]([OH:28])=[O:27])=[O:22])[CH2:15]3)=[O:10])[NH:5][C:6]=1[CH2:7][CH3:8]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 68416710Ethyl trans(+/-)-2-[(5-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-1,3-dihydro-2H-isoindol-2-yl)carbonyl]cyclopropanecarboxylate

Product 1

HCID 68416690trans(+/-)-2-[(5-{[(4-Chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-1,3-dihydro-2H-isoindol-2-yl) carbonyl]cyclopropanecarboxylic acidYield 69%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Ethyl trans(±)-2-[(5-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-1,3-dihydro-2H-isoindol-2-yl)carbonyl]cyclopropanecarboxylate obtained in Example (93a) (0.11 g, 0.26 mmol) was dissolved in methanol (5 mL) and dichloromethane (2 mL). The solution was subjected to the same operation as in Example (91d) using a 2 N aqueous lithium hydroxide solution (2 mL, 4 mmol), to obtain 71 mg of the title compound as a light brown solid (69%).

Sources & evidence

ORD record
ord-705589b8680645bfaf7bc1797069e7fb
Source dataset
uspto-grants-2015_01
Patent number
US08927588B2

Reaction notes

Loading…