Dicyclohexylcarbodiimide → HCID 86744118, compound

HRID 2166346Notes

Reaction equation

HRID 2166346 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[F:16][C:17]1[CH:22]=[CH:21][C:20]([CH:23]2[CH2:27][N:26]([CH2:28][C:29]([OH:31])=[O:30])[C:25](=[O:32])[CH2:24]2)=[CH:19][CH:18]=1.O[N:34]1[C:38](=[O:39])[CH2:37][CH2:36][C:35]1=[O:40]>O1CCOCC1>[F:16][C:17]1[CH:18]=[CH:19][C:20]([CH:23]2[CH2:27][N:26]([CH2:28][C:29]([O:31][N:34]3[C:38](=[O:39])[CH2:37][CH2:36][C:35]3=[O:40])=[O:30])[C:25](=[O:32])[CH2:24]2)=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 21667428HCID 21667428, compound

Product 1

HCID 86744118HCID 86744118, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A total of 31.5 g (150 mmol) of dicyclohexylcarbodiimide is added in portions to a solution of 35.6 g (150 mmol) of 2-[4-(p-fluorophenyl)-2-oxopyrrolidin-1-yl]-acetic acid and 17.2 g (150 mmol) of N-hydroxysuccinimide in 570 ml of dioxan, during which operation the temperature of the reaction mixture should be maintained below 30° by cooling in an ice bath. When the exothermic reaction has ceased, the reaction mixture is stirred for 16 hours at room temperature, the precipitated dicyclohexylurea is filtered off and the filtrate is concentrated to dryness by evaporation under reduced pressure at 70°. The residue is dissolved in 200 ml of ethyl acetate, and diethyl ether is added until the solution starts to turn cloudy. The crystalline precipitate which forms directly is filtered off with suction, washed with diethyl ether and dried. N-[4-(p-fluorophenyl)-2-oxopyrrolidin-1-ylacetoxy]-succinimide having a melting point of 120°-123° is obtained.

Workup

  1. temperatureshould be maintained below 30°
  2. temperatureby cooling in an ice bath
  3. customWhen the exothermic reaction
  4. filtrationthe precipitated dicyclohexylurea is filtered off
  5. concentrationthe filtrate is concentrated to dryness by evaporation under reduced pressure at 70°
  6. dissolutionThe residue is dissolved in 200 ml of ethyl acetate
  7. additiondiethyl ether is added until the solution
  8. filtrationThe crystalline precipitate which forms directly is filtered off with suction
  9. washwashed with diethyl ether
  10. customdried

Sources & evidence

ORD record
ord-e3fd2ba23758408aa820820fbdaf28d0
Source dataset
uspto-grants-1990_07
Patent number
US04945092

Reaction notes

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