Diethyl Oxalate → HCID 86709896, compound

HRID 929485Notes

Reaction equation

HRID 929485 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:17])[CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:4][CH:3]=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:3]=[CH:4][C:5]([N:8]2[C:9](=[O:17])[C:10]([C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=3)=[C:22]([OH:23])[C:21]2=[O:20])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 7268Diethyl OxalateHCID 723395N-(4-chlorophenyl)-2-phenylacetamideHCID 23665647Potassium tert-butoxide

Product 1

HCID 86709896HCID 86709896, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

After the addition of anhydride THF (20 ml) to compound 5d (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 and solvents were removed. Crude purification was carried out by the column chromatography but the next reaction was followed since the purified compound was small in quantity.

Workup

  1. customwas adjusted to 0° C
  2. extractionThree times extractions
  3. customWater was removed
  4. customwere removed
  5. customCrude purification
  6. customthe next reaction

Sources & evidence

ORD record
ord-9efd6477fa3749779e2689f7b7d7a725
Source dataset
uspto-grants-2016_03
Patent number
US09296690B2

Reaction notes

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