Diethylethanolamine → N-Decyl-3-(3-[4-(2-[N,N-diethylamino]ethoxycarbonyl)-2-oxo-pyrrolidino]phenyl)propenamide

HRID 66798

Reaction equation

HRID 66798 reaction equation
[CH2:1]([NH:11][C:12](=[O:30])[CH:13]=[CH:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([N:21]2[CH2:25][CH:24]([C:26]([OH:28])=[O:27])[CH2:23][C:22]2=[O:29])[CH:16]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].C(N1C=CN=C1)(N1C=CN=C1)=O.[CH2:43]([N:45]([CH2:48][CH2:49]O)[CH2:46][CH3:47])[CH3:44]>O1CCCC1>[CH2:1]([NH:11][C:12](=[O:30])[CH:13]=[CH:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([N:21]2[CH2:25][CH:24]([C:26]([O:28][CH2:44][CH2:43][N:45]([CH2:48][CH3:49])[CH2:46][CH3:47])=[O:27])[CH2:23][C:22]2=[O:29])[CH:16]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

5

Reactant 3

HCID 7497Diethylethanolamine2×HCID 682631,1'-CarbonyldiimidazoleHCID 53878346N-Decyl-3-[3-(4-carboxy-2-oxo-pyrrolidino)phenyl]propenamide

Product 1

HCID 53877985N-Decyl-3-(3-[4-(2-[N,N-diethylamino]ethoxycarbonyl)-2-oxo-pyrrolidino]phenyl)propenamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 829 mg. of N-decyl-3-(3-[4-carboxy-2-oxo-pyrrolidino]phenyl)propenamide in 25 ml. of tetrahydrofuran was added 357 mg. of carbonyldiimidazole. The mixture was heated under reflux for 10 minutes, and then 258 mg. of 2-(N,N-diethylamino)ethanol was added. The mixture was again heated under reflux for 10 minutes, and then an additional 258 mg. of 2-(N,N-diethylamino)ethanol was added. The mixture was heated under reflux for 15 minutes and then it was cooled to room temperature. The solvent was removed by evaporation in vacuo, and the residue was dissolved in 75 ml. of ethyl acetate. The ethyl acetate solution was washed successively with water, 1 N sodium hydroxide, water and saturated sodium chloride solution. The ethyl acetate solution was then dried using sodium sulfate, and the ethyl acetate was removed by evaporation in vacuo. The residue (960 mg.) was recrystallized from isopropyl ether giving 570 mg. of the title compound, m.p. 78°-80° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 10 minutes
  3. temperatureThe mixture was again heated
  4. temperatureunder reflux for 10 minutes
  5. temperatureThe mixture was heated
  6. temperatureunder reflux for 15 minutes
  7. customThe solvent was removed by evaporation in vacuo
  8. dissolutionthe residue was dissolved in 75 ml
  9. washThe ethyl acetate solution was washed successively with water, 1 N sodium hydroxide, water and saturated sodium chloride solution
  10. dry with materialThe ethyl acetate solution was then dried
  11. customthe ethyl acetate was removed by evaporation in vacuo
  12. customThe residue (960 mg.) was recrystallized from isopropyl ether giving 570 mg

Sources & evidence

ORD record
ord-3857bd8cf78a4782ba6b7bc50758fb4c
Source dataset
uspto-grants-1982_08
Patent number
US04343813

Linked notes

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