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-benzyl ester

HRID 2065423Notes

Reaction equation

HRID 2065423 reaction equation
C[O:2][C:3]([C:5]1[CH:42]=[CH:41][C:8]([CH2:9][O:10][C:11]([N:13]2[CH2:17][CH:16]([CH2:18][C:19]([CH3:22])([CH3:21])[CH3:20])[C:15]3([C:30]4[C:25](=[CH:26][C:27]([Cl:31])=[CH:28][CH:29]=4)[NH:24][C:23]3=[O:32])[CH:14]2[C:33]2[CH:38]=[CH:37][CH:36]=[C:35]([Cl:39])[C:34]=2[F:40])=[O:12])=[CH:7][CH:6]=1)=[O:4].[Li+].[OH-].CO>O1CCCC1.O>[C:3]([C:5]1[CH:42]=[CH:41][C:8]([CH2:9][O:10][C:11]([N:13]2[CH2:17][CH:16]([CH2:18][C:19]([CH3:22])([CH3:21])[CH3:20])[C:15]3([C:30]4[C:25](=[CH:26][C:27]([Cl:31])=[CH:28][CH:29]=4)[NH:24][C:23]3=[O:32])[CH:14]2[C:33]2[CH:38]=[CH:37][CH:36]=[C:35]([Cl:39])[C:34]=2[F:40])=[O:12])=[CH:7][CH:6]=1)([OH:4])=[O:2]

Participants

6

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 67337493rac-(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-benzyl ester

Product 1

HCID 67337330rac-(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-benzyl 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-benzyl ester (50 mg, 0.08 mmol) was heated with aqueous LiOH (19 mg, 0.8 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-benzyl ester as a white solid (Yield, 35 mg, 71%).

Workup

  1. customto give

Sources & evidence

ORD record
ord-845da4dd0df8488f98b320f033da9803
Source dataset
uspto-grants-2012_10
Patent number
US08288431B2

Reaction notes

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