Diethyl Oxalate → HCID 86709894, compound

HRID 929483Notes

Reaction equation

HRID 929483 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:17])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C([O:20][C:21](=O)[C:22](OCC)=[O:23])C.CC(C)([O-])C.[K+]>O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:9](=[O:17])[C:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[C:22]([OH:23])[C:21]1=[O:20]

Participants

5

Reactant 3

HCID 7268Diethyl OxalateHCID 364845N-(2-Chlorophenyl)-2-phenylacetamideHCID 23665647Potassium tert-butoxide

Product 1

HCID 86709894HCID 86709894, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

After the addition of anhydride THF (20 ml) to compound 5b (1.40 g, 7.34 mmol), the temperature was adjusted to 0° C. Diethyloxalate (1.45 g, 9.50 mmol) and potassium t-butoxide (1.35 g, 11.9 mmol) were added thereto and the agitation for 3 hours was carried out. After the identification of the reaction progress with TLC, the solution was poured into the distilled water and acidified with 1N HCL aqueous solution. Three times extractions were carried out with EA and three times washings were carried out with brine. Water was removed by using Na2SO4, solvents were removed and then, crude purification was carried out by the column chromatography (EA/HX, ⅕).

Workup

  1. customwas adjusted to 0° C
  2. extractionThree times extractions
  3. customWater was removed
  4. customwere removed
  5. customcrude purification

Sources & evidence

ORD record
ord-f51ae69204c24faeaa80f428f5bee4af
Source dataset
uspto-grants-2016_03
Patent number
US09296690B2

Reaction notes

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