Potassium Carbonate → 6-chloro-4'-[5-chloro-2-(2-methanesulfonylamino-1,1-diethyl-2-oxo-ethoxy)-phenyl]-2'-(5-fluoro-2-methyl-phenyl)-6'-thioxo spiro[3H-indole-3,3'-piperidine]-2(1H)-one

HRID 658919Notes

Reaction equation

HRID 658919 reaction equation
C([N:4]1[C:46]2[C:41](=[CH:42][CH:43]=[C:44]([Cl:47])[CH:45]=2)[C:6]2([CH:11]([C:12]3[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:13]=3[O:19][C:20]([CH2:30][CH3:31])([CH2:28][CH3:29])[C:21]([NH:23][S:24]([CH3:27])(=[O:26])=[O:25])=[O:22])[CH2:10][C:9](=[S:32])[NH:8][CH:7]2[C:33]2[CH:38]=[C:37]([F:39])[CH:36]=[CH:35][C:34]=2[CH3:40])[C:5]1=[O:48])(=O)C.C([O-])([O-])=O.[K+].[K+]>CO>[Cl:47][C:44]1[CH:45]=[C:46]2[NH:4][C:5](=[O:48])[C:6]3([CH:11]([C:12]4[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:13]=4[O:19][C:20]([CH2:30][CH3:31])([CH2:28][CH3:29])[C:21]([NH:23][S:24]([CH3:27])(=[O:25])=[O:26])=[O:22])[CH2:10][C:9](=[S:32])[NH:8][CH:7]3[C:33]3[CH:38]=[C:37]([F:39])[CH:36]=[CH:35][C:34]=3[CH3:40])[C:41]2=[CH:42][CH:43]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 723235021-acetyl-6-chloro-4'-[5-chloro-2-(2-methanesulfonylamino-1,1-diethyl-2-oxo-ethoxy)-phenyl]-2'-(5-fluoro-2-methyl-phenyl)-6'-thioxo spiro[3H-indole-3,3'-piperidine]-2(1H)-one

Product 1

HCID 752933816-chloro-4'-[5-chloro-2-(2-methanesulfonylamino-1,1-diethyl-2-oxo-ethoxy)-phenyl]-2'-(5-fluoro-2-methyl-phenyl)-6'-thioxo spiro[3H-indole-3,3'-piperidine]-2(1H)-oneYield 82.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of chiral (2′S, 3S, 4′R)-1-acetyl-6-chloro-4′-[5-chloro-2-(2-methanesulfonylamino-1,1-diethyl-2-oxo-ethoxy)-phenyl]-2′-(5-fluoro-2-methyl-phenyl)-6′-thioxo spiro[3H-indole-3,3′-piperidine]-2(1H)-one (45 mg) and K2CO3 (30 mg) in methanol (2 mL) was stirred at room temperature for 15 min, and then the mixture was partitioned between ethyl acetate and diluted aqueous HCl solution. The organic layer was washed with brine, dried over anhydrous Na2SO4, concentrated to give the title compound as white solid (35 mg).

Workup

  1. customthe mixture was partitioned between ethyl acetate and diluted aqueous HCl solution
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-8d27308e3cf0456096599f77fc5148ff
Source dataset
uspto-grants-2011_12
Patent number
US08076482B2

Reaction notes

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