Water → ethyl (2Z)-2-(2-oxopyrrolidin-3-yl)oxyimino-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetate

HRID 1252321Notes

Reaction equation

HRID 1252321 reaction equation
[C:1]([NH:20][C:21]1[S:22][CH:23]=[C:24](/[C:26](=[N:32]/[OH:33])/[C:27]([O:29][CH2:30][CH3:31])=[O:28])[N:25]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH:41]1[CH2:45][CH2:44][NH:43][C:42]1=[O:46].O>CS(C)=O>[C:1]([NH:20][C:21]1[S:22][CH:23]=[C:24](/[C:26](=[N:32]/[O:33][CH:41]2[CH2:45][CH2:44][NH:43][C:42]2=[O:46])/[C:27]([O:29][CH2:30][CH3:31])=[O:28])[N:25]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 6410761(Z)-Ethyl 2-(hydroxyimino)-2-(2-(tritylamino)thiazol-4-yl)acetateHCID 101034713-Bromopyrrolidin-2-one

Product 1

HCID 13335552ethyl (2Z)-2-(2-oxopyrrolidin-3-yl)oxyimino-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetateYield 85.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

15.8 g of ethyl (Z)-2-(2-tritylaminothiazol-4-yl)-2-hydroxyiminoacetate are dissolved in 70 ml of dimethylsulfoxide, and 5.8 g of anhydrous potassium carbonate are added thereto. The mixture is stirred at room temperature for 20 minutes. 6.6 g of 3-bromo-2-pyrrolidone are added to said mixture, and the mixture is stirred at room temperature for 20 hours. The mixture is poured into 800 ml of water, and crystalline precipitates are collected by filtration and washed with water. The crystals are dissolved in chloroform, washed with water and then dried. Then, the chloroform solution is evaporated under reduced pressure to remove solvent. 100 ml of ethyl acetate was added to the residue, and allowed to stand at room temperature. Crystalline precipitates thus obtained are collected by filtration and dried. 16.0 g of ethyl (Z)-2-(2-tritylaminothiazol-4-yl)-2-[(2-pyrrolidon-3-yl)oxyimino]acetate are obtained.

Workup

  1. stirringthe mixture is stirred at room temperature for 20 hours
  2. customcrystalline precipitates
  3. filtrationare collected by filtration
  4. washwashed with water
  5. dissolutionThe crystals are dissolved in chloroform
  6. washwashed with water
  7. customdried
  8. customThen, the chloroform solution is evaporated under reduced pressure
  9. customto remove solvent
  10. addition100 ml of ethyl acetate was added to the residue
  11. customto stand at room temperature
  12. customCrystalline precipitates thus
  13. customobtained
  14. filtrationare collected by filtration
  15. customdried

Sources & evidence

ORD record
ord-4b23f218422949bf986bda2f6c00124b
Source dataset
uspto-grants-1988_05
Patent number
US04742174

Reaction notes

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