Lithium hydroxide, monohydrate → HCID 51356968, compound

HRID 909078Notes

Reaction equation

C([O:3][C:4](=[O:37])[CH2:5][NH:6][C:7]([N:9]1[CH2:13][C@@H:12]([CH2:14][C:15]([CH3:18])([CH3:17])[CH3:16])[C@@:11]([C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=2[F:28])([C:19]#[N:20])[C@H:10]1[C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([Cl:35])[C:30]=1[F:36])=[O:8])C.O.[OH-].[Li+]>>[Cl:35][C:31]1[C:30]([F:36])=[C:29]([C@@H:10]2[C@:11]([C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=3[F:28])([C:19]#[N:20])[C@H:12]([CH2:14][C:15]([CH3:17])([CH3:18])[CH3:16])[CH2:13][N:9]2[C:7]([NH:6][CH2:5][C:4]([OH:37])=[O:3])=[O:8])[CH:34]=[CH:33][CH:32]=1

Participants

Reactant 2

HCID 168937Lithium hydroxide, monohydrate

HCID 51356693HCID 51356693, compound

Product 1

HCID 51356968HCID 51356968, compoundYield 94%

Procedure

In a manner similar to the method described in Example 52, rac-{[(2S,3S,4S)-2-(3-chloro-2-fluoro-phenyl)-3-(4-chloro-2-fluoro-phenyl)-3-cyano-4-(2,2-dimethyl-propyl)-pyrrolidine-1-carbonyl]-amino}-acetic acid ethyl ester (83 mg, 0.144 mmol, example C16) was reacted with lithium hydroxide hydrate (36 mg, 0.945 mmol, Aldrich) to give rac-{[(2S,3S,4S)-2-(3-chloro-2-fluoro-phenyl)-3-(4-chloro-2-fluoro-phenyl)-3-cyano-4-(2,2-dimethyl-propyl)-pyrrolidine-1-carbonyl]-amino}-acetic acid (71 mg, 92%) HRMS (ES+) m/z Calcd for C25H25Cl2F2N3O3+H [(M+H)+]: 524.1314; Found: 524.1315.

Sources & evidence

ORD record: ord-8fc337f431274cf6ab97d1e4668dc3a5
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08017607B2

Reaction notes

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