Methanol → rac-(2'S,3'S,4'S)-6-chloro-2'-(3-chloro-2-fluoro-phenyl)-4'-(2,2-dimethyl-propyl)-2-oxo-1,2-dihydro-spiro[indole-3,3'-pyrrolidine]-1'-carboxylic acid 4-carboxy-phenyl ester

HRID 2065430Notes

Reaction equation

HRID 2065430 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][C:12]([N:14]2[CH2:18][CH:17]([CH2:19][C:20]([CH3:23])([CH3:22])[CH3:21])[C:16]3([C:31]4[C:26](=[CH:27][C:28]([Cl:32])=[CH:29][CH:30]=4)[NH:25][C:24]3=[O:33])[CH:15]2[C:34]2[CH:39]=[CH:38][CH:37]=[C:36]([Cl:40])[C:35]=2[F:41])=[O:13])=[CH:7][CH:6]=1)=[O:4].[Li+].[OH-].CO>O1CCCC1.O>[C:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][C:12]([N:14]2[CH2:18][CH:17]([CH2:19][C:20]([CH3:23])([CH3:22])[CH3:21])[C:16]3([C:31]4[C:26](=[CH:27][C:28]([Cl:32])=[CH:29][CH:30]=4)[NH:25][C:24]3=[O:33])[CH:15]2[C:34]2[CH:39]=[CH:38][CH:37]=[C:36]([Cl:40])[C:35]=2[F:41])=[O:13])=[CH:7][CH:6]=1)([OH:4])=[O:2]

Participants

6

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 67337314rac-(2'S,3'S,4'S)-6-chloro-2'-(3-chloro-2-fluoro-phenyl)-4'-(2,2-dimethyl-propyl)-2-oxo-1,2-dihydro-spiro[indole-3,3'-pyrrolidine]-1'-carboxylic acid 4-methoxycarbonyl-phenyl ester

Product 1

HCID 67337713rac-(2'S,3'S,4'S)-6-chloro-2'-(3-chloro-2-fluoro-phenyl)-4'-(2,2-dimethyl-propyl)-2-oxo-1,2-dihydro-spiro[indole-3,3'-pyrrolidine]-1'-carboxylic acid 4-carboxy-phenyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

In a manner similar to the method described in Example 13, rac-(2′S,3′S,4′S)-6-chloro-2′-(3-chloro-2-fluoro-phenyl)-4′-(2,2-dimethyl-propyl)-2-oxo-1,2-dihydro-spiro[indole-3,3′-pyrrolidine]-1′-carboxylic acid 4-methoxycarbonyl-phenyl ester (10 mg, 0.02 mmol) was heated with aqueous LiOH (4 mg, 0.2 mmol) in tetrahydrofuran (3 mL), water (3 mL), and methanol (1 mL) at room temperature for 18 h to give rac-(2′S,3′S,4′S)-6-chloro-2′-(3-chloro-2-fluoro-phenyl)-4′-(2,2-dimethyl-propyl)-2-oxo-1,2-dihydro-spiro[indole-3,3′-pyrrolidine]-1′-carboxylic acid 4-carboxy-phenyl ester as a white solid (Yield, 8 mg, 82%).

Workup

  1. customto give

Sources & evidence

ORD record
ord-9f95590469ae44e29c54a2fc2a87a1f6
Source dataset
uspto-grants-2012_10
Patent number
US08288431B2

Reaction notes

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