Water → 2-{[4-(2-Ethoxy-2-oxoethyl)-1,3-thiazol-2-yl]thio}-2-methylpropionic acid tert-butyl ester

HRID 914282Notes

Reaction equation

HRID 914282 reaction equation
[CH2:1]([O:3][C:4](=[O:12])[CH2:5][C:6]1[N:7]=[C:8]([SH:11])[S:9][CH:10]=1)[CH3:2].Br[C:14]([CH3:23])([CH3:22])[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[C:18]([O:17][C:15](=[O:16])[C:14]([S:11][C:8]1[S:9][CH:10]=[C:6]([CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:12])[N:7]=1)([CH3:23])[CH3:22])([CH3:21])([CH3:20])[CH3:19]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 90290tert-Butyl 2-bromo-2-methylpropionateHCID 178470768HCID 178470768, compound

Product 1

HCID 597588642-{[4-(2-Ethoxy-2-oxoethyl)-1,3-thiazol-2-yl]thio}-2-methylpropionic acid tert-butyl esterYield 99.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(2-Mercapto-1,3-thiazol-4-yl)acetic acid ethyl ester (88.6 g) synthesized in Example 1 and tert-butyl 2-bromo-2-methylpropionate (105.3 g) were dissolved in N,N-dimethylformamide (700 mL), potassium carbonate (66.3 g) was added, and the mixture was stirred at room temperature for 8 hr. Water (1 L) was added to the reaction mixture, and the mixture was extracted with ethyl acetate (1 L). The organic layer was washed with saturated brine, and dried over hydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give the title compound (150 g) as a slightly brown oil. The present compound was used in the next step without particular purification.

Workup

  1. extractionthe mixture was extracted with ethyl acetate (1 L)
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over hydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-37aedf2e25be475abed08cfa18ad2c52
Source dataset
uspto-grants-2011_09
Patent number
US08026370B2

Reaction notes

Loading…