Water → HCID 88404739, compound

HRID 2309579Notes

Reaction equation

HRID 2309579 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:18]/[OH:19])/[C:8]([O:10][CH2:11][CH2:12][S:13]([CH2:16][CH3:17])(=[O:15])=[O:14])=[O:9])[N:6]=1.Br[CH2:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23].O.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:18]/[O:19][CH2:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])/[C:8]([O:10][CH2:11][CH2:12][S:13]([CH2:16][CH3:17])(=[O:14])=[O:15])=[O:9])[N:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 88404508HCID 88404508, compound

Product 1

HCID 88404739HCID 88404739, compoundYield 74.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
40 °C

Procedure

In 180 ml of acetone was suspended 6 g (0.019 mole) of ethylsulfonylethyl 2-(2-aminothiazol-4-yl)-(Z)-2-hydroxyiminoacetate as obtained in Example 9 followed by a serial addition of 5.7 g (0.0292 mole) of t-butyl bromoacetate, 0.9 ml of water and 10.8 g of anhydrous potassium carbonate. The mixture was stirred at 40° C. for 2 hours and the insoluble matter was filtered off. To the filtrate was added 200 ml of water and 200 ml of ethyl acetate was added to extract the reaction product. The aqueous layer was further extracted with ethyl acetate. The organic layers were combined, washed with water and concentrated to dryness under reduced pressure to give 6.0 g of ethylsulfonylethyl 2-(2-aminothiazol-4-yl)-(Z)-2-(t-butoxycarbonylmethoxyimino)acetate as white crystals. (Yield, 73.0%)

Workup

  1. customas obtained in Example 9
  2. filtrationthe insoluble matter was filtered off
  3. additionTo the filtrate was added 200 ml of water and 200 ml of ethyl acetate
  4. additionwas added
  5. extractionto extract the reaction product
  6. extractionThe aqueous layer was further extracted with ethyl acetate
  7. washwashed with water
  8. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-1dcbe950d26a4d07a73f692bf162560b
Source dataset
uspto-grants-1987_09
Patent number
US04695639

Reaction notes

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