Potassium Carbonate → HCID 10113827, compound

HRID 2084418Notes

Reaction equation

HRID 2084418 reaction equation
[CH2:1]([C:8]1([S:15]([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)(=[O:17])=[O:16])[S:12][C:11](=[O:13])[NH:10][C:9]1=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:27][C:28]([O:30]C(C)(C)C)=[O:29].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:1]([C:8]1([S:15]([C:18]2[CH:19]=[CH:20][C:21]([O:24][CH3:25])=[CH:22][CH:23]=2)(=[O:17])=[O:16])[S:12][C:11](=[O:13])[N:10]([CH2:27][C:28]([OH:30])=[O:29])[C:9]1=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 10270937HCID 10270937, compound

Product 1

HCID 10113827HCID 10113827, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 5-Benzyl-5-(4-methoxybenzenesulfonyl)thiazolidine-2,4-dione (Example 6) (0.740 g, 1.96 mmol) in 34.5 mL of acetone was added t-butyl bromoacetate (4.227 g, 21.67 mmol) and potassium carbonate (2.75 g, 19.90 mmol) and the mixture was stirred for 16 h at room temperature under a nitrogen atmosphere. The mixture was filtered and concentrated in vacuo. Column chromatography provided the t-butyl ester of the title compound as a viscous yellow oil. This material was dissolved in 96 mL of dichloromethane and 17.8 mL of trifluroacetic acid was added and the mixture was stirred 2.5 h at room temperature under a nitrogen atmosphere. The mixture was concentrated in vacuo, triturated with hexane, and filtered. The solid was redissolved in dichloromethane and again concentrated in vacuo to give 0.720 g of the title compound as a beige solid.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-341430a535f042808dfa4e5970bc0409
Source dataset
uspto-grants-2004_04
Patent number
US06716862B2

Reaction notes

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