Lithium hydroxide, monohydrate → HCID 53357487, compound

HRID 1807270Notes

Reaction equation

HRID 1807270 reaction equation
C([O:3][C:4](=[O:43])[C:5]1[CH:10]=[CH:9][C:8]([CH2:11][NH:12][C:13]([C@H:15]2[C@H:19]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[C:21]=3[F:27])[C@:18]([C:30]3[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][C:31]=3[F:37])([C:28]#[N:29])[C@H:17]([CH2:38][C:39]([CH3:42])([CH3:41])[CH3:40])[NH:16]2)=[O:14])=[N:7][CH:6]=1)C.O.[OH-].[Li+]>C1COCC1.O>[Cl:36][C:33]1[CH:34]=[CH:35][C:30]([C@@:18]2([C:28]#[N:29])[C@H:17]([CH2:38][C:39]([CH3:41])([CH3:40])[CH3:42])[NH:16][C@@H:15]([C:13]([NH:12][CH2:11][C:8]3[CH:9]=[CH:10][C:5]([C:4]([OH:43])=[O:3])=[CH:6][N:7]=3)=[O:14])[C@@H:19]2[C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[C:21]=2[F:27])=[C:31]([F:37])[CH:32]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 53357227HCID 53357227, compound

Product 1

HCID 53357487HCID 53357487, compoundYield 101.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

In a manner similar to the method described in Example 380, chiral 6-({[(2R,3S,4R,5S)-4-(4-Chloro-2-fluoro-phenyl)-3-(3-chloro-2-fluoro-phenyl)-4-cyano-5-(2,2-dimethyl-propyl)-pyrrolidine-2-carbonyl]-amino}-methyl)-nicotinic acid ethyl ester (73.8 mg, 0.117 mmol) in THF (8 ml) was combined with lithium hydroxide hydrate (35.9 mg, 0.855 mmol) in water (4 mL). It was stirred at room temperature to give chiral 6-({[(2R,3S,4R,5S)-4-(4-Chloro-2-fluoro-phenyl)-3-(3-chloro-2-fluoro-phenyl)-4-cyano-5-(2,2-dimethyl-propyl)-pyrrolidine-2-carbonyl]-amino}-methyl)-nicotinic acid as a white lyophilized solid (71.3 mg, 100%). HRMS (ES+) m/z Calcd C30H28Cl2F2N4O3+H [(M+H): 601.1580. Found: 601.1581.

Sources & evidence

ORD record
ord-9cefd928003e43ff8397f3328fa43fed
Source dataset
uspto-grants-2013_01
Patent number
US08354444B2

Reaction notes

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