Potassium Hydroxide → rac-[(2S,3R,4S)-4-(3-chloro-2-fluoro-phenyl)-3-(4-chloro-2-fluoro-phenyl)-3-cyano-2-(2,2-dimethyl-propyl)-pyrrolidin-1-yl]-acetic acid

HRID 909061Notes

Reaction equation

HRID 909061 reaction equation
C[O:2][C:3](=[O:33])[CH2:4][N:5]1[CH2:9][C@H:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[C:11]=2[F:17])[C@:7]([C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:21]=2[F:27])([C:18]#[N:19])[C@@H:6]1[CH2:28][C:29]([CH3:32])([CH3:31])[CH3:30].[OH-].[K+]>C1COCC1.CO>[Cl:16][C:12]1[C:11]([F:17])=[C:10]([C@H:8]2[CH2:9][N:5]([CH2:4][C:3]([OH:33])=[O:2])[C@@H:6]([CH2:28][C:29]([CH3:32])([CH3:31])[CH3:30])[C@@:7]2([C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:21]=2[F:27])[C:18]#[N:19])[CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 67095460rac-[(2S,3R,4S)-4-(3-chloro-2-fluoro-phenyl)-3-(4-chloro-2-fluoro-phenyl)-3-cyano-2-(2,2-dimethyl-propyl)-pyrrolidin-1-yl]-acetic acid methyl ester

Product 1

HCID 51355303rac-[(2S,3R,4S)-4-(3-chloro-2-fluoro-phenyl)-3-(4-chloro-2-fluoro-phenyl)-3-cyano-2-(2,2-dimethyl-propyl)-pyrrolidin-1-yl]-acetic acidYield 98%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

In a manner similar to the method described in Example 8, rac-[(2S,3R,4S)-4-(3-chloro-2-fluoro-phenyl)-3-(4-chloro-2-fluoro-phenyl)-3-cyano-2-(2,2-dimethyl-propyl)-pyrrolidin-1-yl]-acetic acid methyl ester (115 mg, 0.23 mmol) in THF/MeOH (1.8/0.6 mL) was treated with 2N KOH (0.6 mL) at rt overnight to give rac-[(2S,3R,4S)-4-(3-chloro-2-fluoro-phenyl)-3-(4-chloro-2-fluoro-phenyl)-3-cyano-2-(2,2-dimethyl-propyl)-pyrrolidin-1-yl]-acetic acid (108.5 mg, 97.0%).

Sources & evidence

ORD record
ord-e62cdf8a65e2488886db0cdf62bc8bd8
Source dataset
uspto-grants-2011_09
Patent number
US08017607B2

Reaction notes

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