Water → HCID 88404618, compound

HRID 2309578Notes

Reaction equation

HRID 2309578 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:17]/[OH:18])/[C:8]([O:10][CH2:11][CH2:12][S:13]([CH3:16])(=[O:15])=[O:14])=[O:9])[N:6]=1.Br[CH:20]([CH3:28])[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22].O.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:17]/[O:18][CH:20]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH3:28])/[C:8]([O:10][CH2:11][CH2:12][S:13]([CH3:16])(=[O:14])=[O:15])=[O:9])[N:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 545327tert-Butyl 2-bromopropanoateHCID 88404401HCID 88404401, compound

Product 1

HCID 88404618HCID 88404618, compoundYield 75.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
40 °C

Procedure

In 100 ml of acetone was suspended 5 g (0.017 mole) of methylsulfonylethyl 2-(2-aminothiazol-4-yl)-(Z)-2-hydroxyiminoacetate and 5.33 g (0.0255 mole) of t-butyl 2-bromopropionate was added. After a serial addition of 0.3 ml of water and 9.4 g of anhydrous potassium carbonate, the mixture was stirred at 40° C. for about 2.5 hours. After completion of the reaction, the insoluble matter was filtered off. To the filtrate was added 100 ml of water and the mixture was extracted with 150 ml of ethyl acetate. The organic layer was washed with 50 ml of saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate. The sodium sulfate was filtered off and the filtrate was concentrated to dryness under reduced pressure. The concentrate was crystallized from ethyl acetate-isopropyl ether (1:5, v/v). After cooling to 0° C. or below, the crystalline precipitate was collected by filtration and dried under reduced pressrue to give 5.4 g (yield, 75.4%) of methylsulfonylethyl 2-(2-aminothiazol-4-yl)-(Z)-2-(t-butoxycarbonyl-1-methylmethoxyimino)acetate as white crystals.

Workup

  1. additionwas added
  2. customAfter completion of the reaction
  3. filtrationthe insoluble matter was filtered off
  4. additionTo the filtrate was added 100 ml of water
  5. extractionthe mixture was extracted with 150 ml of ethyl acetate
  6. washThe organic layer was washed with 50 ml of saturated aqueous sodium chloride solution
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationThe sodium sulfate was filtered off
  9. concentrationthe filtrate was concentrated to dryness under reduced pressure
  10. customThe concentrate was crystallized from ethyl acetate-isopropyl ether (1:5
  11. temperatureAfter cooling to 0° C. or below
  12. filtrationthe crystalline precipitate was collected by filtration
  13. customdried

Sources & evidence

ORD record
ord-38aac1062e5b4c41a8db723066e860d0
Source dataset
uspto-grants-1987_09
Patent number
US04695639

Reaction notes

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