Potassium Carbonate → N-[(S)-1-(4-ethylthiazol-2-yl)-2-(4-nitrophenyl)ethyl]-2-(3-methyl-1,2,4-oxadiazol-5-yl)-3-phenylpropanamide

HRID 1714517Notes

Reaction equation

HRID 1714517 reaction equation
[CH2:1]([CH:8]([C:14]([NH:16][C@H:17]([C:28]1[S:29][CH:30]=[C:31]([CH2:33][CH3:34])[N:32]=1)[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=1)=[O:15])[C:9]([O:11]CC)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[C:41](=[N:44]O)([NH2:43])[CH3:42]>C1(C)C=CC=CC=1>[CH2:33]([C:31]1[N:32]=[C:28]([C@@H:17]([NH:16][C:14](=[O:15])[CH:8]([C:9]2[O:11][N:44]=[C:41]([CH3:42])[N:43]=2)[CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:18][C:19]2[CH:20]=[CH:21][C:22]([N+:25]([O-:27])=[O:26])=[CH:23][CH:24]=2)[S:29][CH:30]=1)[CH3:34]

Participants

5

Reactant 3

HCID 11430Potassium Carbonate2×HCID 30926N-Hydroxyacetamidine2×HCID 59464662Ethyl 2-benzyl-3-((S)-1-(4-ethylthiazol-2-yl)-2-(4-nitrophenyl)ethylamino)-3-oxopropanoate

Product 1

HCID 59464676N-[(S)-1-(4-ethylthiazol-2-yl)-2-(4-nitrophenyl)ethyl]-2-(3-methyl-1,2,4-oxadiazol-5-yl)-3-phenylpropanamideYield 94%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Ethyl 2-benzyl-3-((S)-1-(4-ethylthiazol-2-yl)-2-(4-nitrophenyl)ethylamino)-3-oxopropanoate is dissolved in toluene (5 mL) and heated to reflux. Potassium carbonate (80 mg) and acetamide oxime (43 mg) are added and treated with 80 mg potassium carbonate and 43 mg acetamide oxime at reflux. The reaction mixture is cooled to room temperature, filtered and concentrated. The residue is chromatographed over silica to afford 0.221 g (94%) of the desired product as a yellow oil.

Workup

  1. temperatureheated to reflux
  2. temperatureat reflux
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue is chromatographed over silica

Sources & evidence

ORD record
ord-dcea7dc3959249ecbe6cccc80c67edec
Source dataset
uspto-grants-2010_09
Patent number
US07795444B2

Reaction notes

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