Potassium Carbonate → HCID 15144285, compound

HRID 2232420Notes

Reaction equation

HRID 2232420 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:15]/[OH:16])/[C:8]([O:10][CH2:11][CH2:12][S:13][CH3:14])=[O:9])[N:6]=1.Br[CH:18]([CH2:26][CH3:27])[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:15]/[O:16][CH:18]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:26][CH3:27])/[C:8]([O:10][CH2:11][CH2:12][S:13][CH3:14])=[O:9])[N:6]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 13124118tert-Butyl 2-bromobutanoateHCID 15144281HCID 15144281, compound

Product 1

HCID 15144285HCID 15144285, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 10 g of 2-methylthioethyl 2-(2-aminothiazol-4-yl)-2(Z)-hydroxyiminoacetate, 10 g of tertbutyl 2-bromobutyrate and 7 g of anhydrous potassium carbonate in 250 ml of acetone is kept at 60°-70° C. for 20 hours with stirring. Insolubles are filtered off and the filtrate is concentrated under reduced pressure. The residue is dissolved in ethyl acetate, and the solution is washed with water, then with saturated aqueous sodium chloride and dried over anhydrous magnesium sulfate. The solvent is then evaporated off to give the above-identified compound as a viscous liquid, which, upon standing, solidifies. Yield: 12.6 g.

Workup

  1. filtrationInsolubles are filtered off
  2. concentrationthe filtrate is concentrated under reduced pressure
  3. dissolutionThe residue is dissolved in ethyl acetate
  4. washthe solution is washed with water
  5. dry with materialwith saturated aqueous sodium chloride and dried over anhydrous magnesium sulfate
  6. customThe solvent is then evaporated off

Sources & evidence

ORD record
ord-d2d11511908046d49727f3ac3ac15b44
Source dataset
uspto-grants-1988_11
Patent number
US04788185

Reaction notes

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