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

HRID 745443Notes

Reaction equation

HRID 745443 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+].[CH3:40][N:41]1[CH2:45][CH2:44][CH:43](Br)[C:42]1=[O:47].O>CS(C)=O>[C:1]([NH:20][C:21]1[S:22][CH:23]=[C:24](/[C:26](=[N:32]/[O:33][CH:43]2[CH2:44][CH2:45][N:41]([CH3:40])[C:42]2=[O:47])/[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 111829543-Bromo-1-methylpyrrolidin-2-one

Product 1

HCID 13536859ethyl (2Z)-2-(1-methyl-2-oxopyrrolidin-3-yl)oxyimino-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetateYield 64.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

2.7 g of ethyl (Z)-2-(2-tritylaminothiazol-4-yl)-2hydroxyiminoacetate are dissolved in 12 ml of dimethylsulfoxide, and 1.0 g of anhydrous potassium carbonate is added thereto under nitrogen gas atmosphere. The mixture is stirred at room temperature for 10 minutes. 1.2 g of 1-methyl-3-bromo-2-pyrrolidone are added to the mixture, and the mixture is stirred at room temperature for 5 hours. The reaction mixture is poured into 100 ml of water, and crystalline precipitates are collected by filtration. The crystals are dissolved in ethyl acetate, and the solution is washed with water and then dried. The solution is concentrated under reduced pressure to remove solvent. Then, the residue is crystallized with isopropyl ether and collected by filtration. 2.1 g of ethyl (Z)-2-(2-tritylaminothiazol-4-yl)-2-[(1-methyl-2-pyrrolidon-3-yl)oxyimino]acetate are obtained.

Workup

  1. stirringthe mixture is stirred at room temperature for 5 hours
  2. customcrystalline precipitates
  3. filtrationare collected by filtration
  4. dissolutionThe crystals are dissolved in ethyl acetate
  5. washthe solution is washed with water
  6. customdried
  7. concentrationThe solution is concentrated under reduced pressure
  8. customto remove solvent
  9. customThen, the residue is crystallized with isopropyl ether
  10. filtrationcollected by filtration

Sources & evidence

ORD record
ord-31dd09b906274f6b8f82fef67f94da68
Source dataset
uspto-grants-1986_07
Patent number
US04598154

Reaction notes

Loading…