Potassium Carbonate → Tert-butyl (2-(5-(4-ethoxybenzyl)-2,4-dioxothiazolidin-3-yl)ethyl)carbamate

HRID 517572Notes

Reaction equation

HRID 517572 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7]([O:9][C:10]1[CH:23]=[CH:22][C:13]([CH2:14][CH:15]2[S:19][C:18](=[O:20])[NH:17][C:16]2=[O:21])=[CH:12][CH:11]=1)[CH3:8].Br[CH2:25][CH2:26][NH:27][C:28](=[O:34])[O:29][C:30]([CH3:33])([CH3:32])[CH3:31]>CN(C=O)C>[CH2:7]([O:9][C:10]1[CH:23]=[CH:22][C:13]([CH2:14][CH:15]2[S:19][C:18](=[O:20])[N:17]([CH2:25][CH2:26][NH:27][C:28](=[O:34])[O:29][C:30]([CH3:33])([CH3:32])[CH3:31])[C:16]2=[O:21])=[CH:12][CH:11]=1)[CH3:8]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 4103526tert-Butyl N-(2-bromoethyl)carbamateHCID 443197195-(4-Ethoxybenzyl)thiazolidine-2,4-dione

Product 1

HCID 71697069Tert-butyl (2-(5-(4-ethoxybenzyl)-2,4-dioxothiazolidin-3-yl)ethyl)carbamate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Potassium carbonate (1.40 g, 9.68 mmol) was added to a solution of compound 4 (303 mg, 1.21 mmol) in 4 mL of anhydrous DMF at 0° C. After stifling the reaction mixture for 20 min, a solution of tert-butyl (2-bromoethyl)carbamate (268 mg, 1.21 mmol) in anhydrous DMF (2 mL) was added and then the reaction mixture was stirred at room temperature for 3 h. The reaction was quenched by adding water and then extracted with ethyl acetate. The ethyl acetate layer was washed with 10% NH4Cl aqueous solution followed by water and dried over anhydrous Na2SO4, filtered, concentrated and purified by silica column chromatography (20% ethyl acetate in hexanes) to afford compound 5 in 53.1% (253 mg) as a colorless oil.

Workup

  1. customfor 20 min
  2. customThe reaction was quenched
  3. additionby adding water
  4. extractionextracted with ethyl acetate
  5. washThe ethyl acetate layer was washed with 10% NH4Cl aqueous solution
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. custompurified by silica column chromatography (20% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-0d23888296a2499ba08f913a5279c878
Source dataset
uspto-grants-2015_08
Patent number
US09115122B2

Reaction notes

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