Water → HCID 88404942, compound

HRID 2309580Notes

Reaction equation

HRID 2309580 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:22]/[OH:23])/[C:8]([O:10][CH2:11][CH2:12][S:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)(=[O:15])=[O:14])=[O:9])[N:6]=1.Br[CH2:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27].O.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:22]/[O:23][CH2:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])/[C:8]([O:10][CH2:11][CH2:12][S:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)(=[O:14])=[O:15])=[O:9])[N:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 88404700HCID 88404700, compound

Product 1

HCID 88404942HCID 88404942, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
40 °C

Procedure

In 100 ml of acetone was suspended 5 g (0.0141 mole) of phenylsulfonylethyl 2-(2-aminothiazol-4-yl)-(Z)-2-hydroxyiminoacetate as obtained in Example 11. After a serial addition of 4.0 g (0.0205 mole) of t-butyl bromoacetate, 0.3 ml of water and 7.7 g of anhydrous potassium carbonate, the mixture was stirred at 40° C. for 1.5 hours. After completion of the reaction, the insoluble matter was filtered off and 100 ml of water and 100 ml of ethyl acetate were added to extract the reaction product. The aqueous layer was further extracted with ethyl acetate and the organic layers were combined, washed twice with saturated aqueous sodium chloride and dried over anhydrous sodium sulfate. The solvent was then distilled off under reduced pressure and ethyl acetate-isopropyl ether (1:5, v/v) was added to the residue, whereupon white crystals separated out. After cooling, the crystals were collected by filtration to give 4.1 g (yield, 62%) of phenylsulfonylethyl 2-(2-aminothiazol-4-yl)-(Z)-2-(t-butoxycarbonylmethoxyimino)acetate.

Workup

  1. customas obtained in Example 11
  2. customAfter completion of the reaction
  3. filtrationthe insoluble matter was filtered off
  4. addition100 ml of water and 100 ml of ethyl acetate were added
  5. extractionto extract the reaction product
  6. extractionThe aqueous layer was further extracted with ethyl acetate
  7. washwashed twice with saturated aqueous sodium chloride
  8. dry with materialdried over anhydrous sodium sulfate
  9. distillationThe solvent was then distilled off under reduced pressure and ethyl acetate-isopropyl ether (1:5
  10. additionv/v) was added to the residue, whereupon white crystals
  11. customseparated out
  12. temperatureAfter cooling
  13. filtrationthe crystals were collected by filtration

Sources & evidence

ORD record
ord-e15da95f7f6640b78c4b217801099d7e
Source dataset
uspto-grants-1987_09
Patent number
US04695639

Reaction notes

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