Lithium hydroxide, monohydrate → (R)-4-(1-(1-(4-fluoro-3-methylbenzyl)piperidine-2-carboxamido)cyclopropyl)benzoic acid

HRID 2273134Notes

Reaction equation

HRID 2273134 reaction equation
[F:1][C:2]1[CH:30]=[CH:29][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][CH2:10][CH2:9][C@@H:8]2[C:13]([NH:15][C:16]2([C:19]3[CH:28]=[CH:27][C:22]([C:23]([O:25]C)=[O:24])=[CH:21][CH:20]=3)[CH2:18][CH2:17]2)=[O:14])=[CH:4][C:3]=1[CH3:31].O[Li].O>>[F:1][C:2]1[CH:30]=[CH:29][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][CH2:10][CH2:9][C@@H:8]2[C:13]([NH:15][C:16]2([C:19]3[CH:20]=[CH:21][C:22]([C:23]([OH:25])=[O:24])=[CH:27][CH:28]=3)[CH2:18][CH2:17]2)=[O:14])=[CH:4][C:3]=1[CH3:31]

Participants

3

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 71204755(R)-methyl 4-(1-(1-(4-fluoro-3-methylbenzyl)piperidine-2-carboxamido)cyclopropyl)benzoate

Product 1

HCID 71186191(R)-4-(1-(1-(4-fluoro-3-methylbenzyl)piperidine-2-carboxamido)cyclopropyl)benzoic acidYield 31.7%

Procedure

The title compound (E12) (10.1 mg) was prepared according to the general procedure for esters hydrolysis starting from (R)-methyl 4-(1-(1-(4-fluoro-3-methylbenzyl)piperidine-2-carboxamido)cyclopropyl)benzoate (D29) (33 mg). (LiOH H2O: 3 eq; reaction time: 3 hrs)

Sources & evidence

ORD record
ord-601c8237ea32448199d63925c2f3dfeb
Source dataset
uspto-grants-2015_09
Patent number
US09120824B2

Reaction notes

Loading…