Lithium hydroxide, monohydrate → HCID 51357253, compound

HRID 909090Notes

Reaction equation

C([O:3][C:4](=[O:38])[CH2:5][CH2:6][NH:7][C:8]([N:10]1[CH2:14][C@@H:13]([CH2:15][C:16]([CH3:19])([CH3:18])[CH3:17])[C@@:12]([C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][C:23]=2[F:29])([C:20]#[N:21])[C@H:11]1[C:30]1[CH:35]=[CH:34][CH:33]=[C:32]([Cl:36])[C:31]=1[F:37])=[O:9])C.O.[OH-].[Li+]>>[Cl:36][C:32]1[C:31]([F:37])=[C:30]([C@@H:11]2[C@:12]([C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][C:23]=3[F:29])([C:20]#[N:21])[C@H:13]([CH2:15][C:16]([CH3:18])([CH3:19])[CH3:17])[CH2:14][N:10]2[C:8]([NH:7][CH2:6][CH2:5][C:4]([OH:38])=[O:3])=[O:9])[CH:35]=[CH:34][CH:33]=1

Participants

Reactant 2

HCID 168937Lithium hydroxide, monohydrate

HCID 51357252HCID 51357252, compound

Product 1

HCID 51357253HCID 51357253, compoundYield 99.8%

Procedure

In a manner similar to the method described in Example 8, rac-3-{[(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}-propionic acid ethyl ester (99 mg, 0.175 mmol, example 72) was reacted with lithium hydroxide hydrate (44 mg, 1.047 mmol, Aldrich) to give rac-3-{[(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}-propionic acid (94 mg, 99%). HRMS (ES+) m/z Calcd for C26H27Cl2F2N3O3+H [(M+H)+]: 538.1471; Found: 538.1470.

Sources & evidence

ORD record: ord-912616a6314440808ca98e958377a5cf
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08017607B2

Reaction notes

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