Potassium Carbonate → 2-Methyl-2-{[4-(3-phthalimidopropyl)-1,3-thiazol-2-yl]thio}propionic acid tert-butyl ester

HRID 914290Notes

Reaction equation

HRID 914290 reaction equation
[SH:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][CH2:8][CH2:9][N:10]2[C:14](=[O:15])[C:13]3=[CH:16][CH:17]=[CH:18][CH:19]=[C:12]3[C:11]2=[O:20])[N:6]=1.C(=O)([O-])[O-].[K+].[K+].[C:27]([O:31][C:32](=[O:37])[C:33](Br)([CH3:35])[CH3:34])([CH3:30])([CH3:29])[CH3:28]>CN(C)C=O>[C:27]([O:31][C:32](=[O:37])[C:33]([CH3:35])([S:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][CH2:8][CH2:9][N:10]2[C:11](=[O:20])[C:12]3=[CH:19][CH:18]=[CH:17][CH:16]=[C:13]3[C:14]2=[O:15])[N:6]=1)[CH3:34])([CH3:30])([CH3:29])[CH3:28]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 90290tert-Butyl 2-bromo-2-methylpropionateHCID 178514990HCID 178514990, compound

Product 1

HCID 597588132-Methyl-2-{[4-(3-phthalimidopropyl)-1,3-thiazol-2-yl]thio}propionic acid tert-butyl esterYield 96.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Mercapto-4-(3-phthalimidopropyl)-1,3-thiazole (22.6 g) obtained in Example 31 was dissolved in N,N-dimethylformamide (200 mL), potassium carbonate (11.3 g) and 2-bromo-2-methylpropionic acid tert-butyl ester (17.4 g) were added, and the mixture was stirred at room temperature for 14 hr. The reaction mixture was concentrated under reduced pressure, ethyl acetate and water were added, and the mixture was stirred. The organic layer was dried over magnesium sulfate and evaporated under reduced pressure. The residue was purified by silica gel chromatography (elution solvent; hexane:ethyl acetate=7:3) to give the title compound (32.0 g) as a colorless oil.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, ethyl acetate and water
  2. additionwere added
  3. stirringthe mixture was stirred
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. customevaporated under reduced pressure
  6. customThe residue was purified by silica gel chromatography (elution solvent; hexane:ethyl acetate=7:3)

Sources & evidence

ORD record
ord-c2d858b39436464e9d31335d64f888fa
Source dataset
uspto-grants-2011_09
Patent number
US08026370B2

Reaction notes

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