Benzene → Racemic cis-1,3-dibenzyl-5-ethoxycarbonyl-2-oxoimidazolidine-4-carboxylic acid

HRID 463733Notes

Reaction equation

HRID 463733 reaction equation
[CH2:1]([N:8]1[C@H:12]2[C:13]([O:15][C:16](=[O:17])[C@H:11]2[N:10]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:9]1=[O:25])=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([OH:28])C.[CH:29]1[CH:34]=CC=CC=1>>[CH2:1]([N:8]1[C@H:12]([C:13]([O:14][CH2:34][CH3:29])=[O:28])[C@H:11]([C:16]([OH:15])=[O:17])[N:10]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:9]1=[O:25])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 241BenzeneHCID 702EthanolHCID 106168311H-Furo[3,4-d]imidazole-2,4,6(3H)-trione, dihydro-1,3-bis(phenylmethyl)-, (3aR,6aS)-rel-

Product 1

HCID 13255428Racemic cis-1,3-dibenzyl-5-ethoxycarbonyl-2-oxoimidazolidine-4-carboxylic acid

Procedure

A mixture of cis-1,3-dibenzyl-2-oxoimidazolidine-4,5-dicarboxylic acid anhydride (70.0 g), 99.5% ethanol (16.6 g) and benzene (1000 ml) was heated under reflux for 2 hours. The reaction mixture (about 600 ml) was concentrated under ordinary pressure. The residue was stirred overnight with n-hexane (200 ml). Crystals produced were filtered and dried under reduced pressure to yield racemic cis-1,3-dibenzyl-5-ethoxycarbonyl-2-oxoimidazolidine-4-carboxylic acid (76.2 g), which were recrystallized from toluene. M.P. 110°-111° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hours
  3. concentrationThe reaction mixture (about 600 ml) was concentrated under ordinary pressure
  4. customCrystals produced
  5. filtrationwere filtered
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-13ab4cfd02084f93af7a227d616f6da7
Source dataset
uspto-grants-1985_10
Patent number
US04544635

Reaction notes

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