Water → ethyl (2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-[(3S)-2-oxopyrrolidin-3-yl]oxyiminoacetate

HRID 414798Notes

Reaction equation

HRID 414798 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:13]/[OH:14])/[C:8]([O:10][CH2:11][CH3:12])=[O:9])[N:6]=1.[C:15](=[O:18])([O-])[O-].[K+].[K+].O>CS(C)=O>[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:13]/[O:14][C@H:8]2[CH2:7][CH2:5][NH:6][C:15]2=[O:18])/[C:8]([O:10][CH2:11][CH3:12])=[O:9])[N:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 6401018Ethyl 2-amino-alpha-(hydroxyimino)thiazol-4-acetate

Product 1

HCID 13536831ethyl (2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-[(3S)-2-oxopyrrolidin-3-yl]oxyiminoacetate

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

1.07 g of ethyl (Z)-2-(2-aminothiazol-4-yl)-2-hydroxyiminoacetate are dissolved in 5 ml of dimethylsulfoxide, and one g of potassium carbonate and 1.53 g of (R)-3-(p-tosyloxy)-2-pyrrolidone are added thereto. The mixture is stirred at room temperature overnight. Water is added to the reaction mixture, and the aqueous mixture is extracted with chloroform. The extract is washed with water, dried and then concentrated under reduced pressure to dryness. The residue is crystallized with isopropyl ether, and the crystals are recrystallized from aqueous methanol. 0.86 g of ethyl (Z)-2-(2-aminothiazol-4-yl)-2-[((3S)-2-pyrrolidon-3-yl)oxyimino]acetate is obtained. The physico-chemical properties of this product are identical with those of the product obtained in Example 1-(2).

Workup

  1. extractionthe aqueous mixture is extracted with chloroform
  2. washThe extract is washed with water
  3. customdried
  4. concentrationconcentrated under reduced pressure to dryness
  5. customThe residue is crystallized with isopropyl ether
  6. customthe crystals are recrystallized from aqueous methanol

Sources & evidence

ORD record
ord-b2232ac0c0ca4569bb91b9dc0e7c557b
Source dataset
uspto-grants-1988_12
Patent number
US04794186

Reaction notes

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