Potassium Carbonate → Ethyl (Z)-alpha-((2-(tert-butoxy)-1,1-dimethyl-2-oxoethoxy)imino)-2-(tritylamino)thiazol-4-acetate

HRID 1590270Notes

Reaction equation

HRID 1590270 reaction equation
[OH:1]/[N:2]=[C:3](/[C:9]1[N:10]=[C:11]([NH:14][C:15]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[S:12][CH:13]=1)\[C:4]([O:6][CH2:7][CH3:8])=[O:5].C(=O)([O-])[O-].[K+].[K+].[C:40]([O:44][C:45](=[O:50])[C:46](Br)([CH3:48])[CH3:47])([CH3:43])([CH3:42])[CH3:41]>CS(C)=O>[C:40]([O:44][C:45]([C:46]([O:1]/[N:2]=[C:3](/[C:9]1[N:10]=[C:11]([NH:14][C:15]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[S:12][CH:13]=1)\[C:4]([O:6][CH2:7][CH3:8])=[O:5])([CH3:48])[CH3:47])=[O:50])([CH3:43])([CH3:42])[CH3:41]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 90290tert-Butyl 2-bromo-2-methylpropionateHCID 6410761(Z)-Ethyl 2-(hydroxyimino)-2-(2-(tritylamino)thiazol-4-yl)acetate

Product 1

HCID 12822365Ethyl (Z)-alpha-((2-(tert-butoxy)-1,1-dimethyl-2-oxoethoxy)imino)-2-(tritylamino)thiazol-4-acetateYield 74.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To ethyl (Z)-2-(hydroxyimino)-2-[2-(triphenylmethyl)aminothiazol-4-yl]acetate (46 g) were added potassium carbonate (27.6 g), tert-butyl-2-bromo-2-methylpropionate(24.1 g) and dimethylsulfoxide (300 ml), and then the solution was stirred for 6 hours at room temperature. Afterwards distilled water (100 ml) was added therein, the solution was stirred again for an hour. The precipitates were filtered, washed with distilled water(500 ml), and dried under reduced pressure to give the above-indicated compound(45.1 g) as a white solid.

Workup

  1. distillationAfterwards distilled water (100 ml)
  2. additionwas added
  3. stirringthe solution was stirred again for an hour
  4. filtrationThe precipitates were filtered
  5. washwashed with distilled water(500 ml)
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-23b749df836d4d2bb0d67a995540b276
Source dataset
uspto-grants-1993_04
Patent number
US05202315

Reaction notes

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