Potassium Carbonate → (Z)-tert-butyl (3-(5-(4-ethoxybenzylidene)-2,4-dioxothiazolidin-3-yl)propyl)carbamate

HRID 517579Notes

Reaction equation

HRID 517579 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7]([O:9][C:10]1[CH:23]=[CH:22][C:13](/[CH:14]=[C:15]2/[C:16](=[O:21])[NH:17][C:18](=[O:20])[S:19]/2)=[CH:12][CH:11]=1)[CH3:8].Br[CH2:25][CH2:26][CH2:27][NH:28][C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32]>CN(C=O)C>[CH2:7]([O:9][C:10]1[CH:23]=[CH:22][C:13](/[CH:14]=[C:15]2/[C:16](=[O:21])[N:17]([CH2:25][CH2:26][CH2:27][NH:28][C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32])[C:18](=[O:20])[S:19]/2)=[CH:12][CH:11]=1)[CH3:8]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 4460490tert-butyl N-(3-bromopropyl)carbamateHCID 5878179(Z)-5-(4-ethoxybenzylidene)thiazolidine-2,4-dione

Product 1

HCID 71697170(Z)-tert-butyl (3-(5-(4-ethoxybenzylidene)-2,4-dioxothiazolidin-3-yl)propyl)carbamateYield 79.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Potassium carbonate (350 mg, 2.53 mmol) was added to a solution of compound 2 (210 mg, 0.84 mmol) in 4 mL of anhydrous DMF at 0° C. After stirring of reaction mixture for 20 min, a solution of tert-butyl (3-bromopropyl)carbamate (200 mg, 0.84 mmol) in anhydrous DMF (3 mL) was added and then the reaction mixture was stirred at room temperature for 3 h. The reaction was quenched by adding water and 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 21a (78.8%, 270 mg) as a white solid.

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 3 h
  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-f053558217e448b98394cb81c60ef7ff
Source dataset
uspto-grants-2015_08
Patent number
US09115122B2

Reaction notes

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