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

HRID 2413390Notes

Reaction equation

HRID 2413390 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.C1C=CC=CC=1.[CH:32]([OH:35])([CH3:34])[CH3:33]>>[CH2:1]([N:8]1[C@H:12]([C:13]([O:35][CH:32]([CH3:34])[CH3:33])=[O:14])[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 3776IsopropanolHCID 106168311H-Furo[3,4-d]imidazole-2,4,6(3H)-trione, dihydro-1,3-bis(phenylmethyl)-, (3aR,6aS)-rel-

Product 1

HCID 13338175Racemic cis-1,3-dibenzyl-5-isopropoxycarbonyl-2-oxoimidazolidine-4-carboxylic acidYield 48.5%

Procedure

A mixture of cis-1,3-dibenzyl-2-oxoimidazolidine-4,5-dicarboxylic acid anhydride (16.8 g), benzene (230 ml) and isopropanol (5.50 g) was refluxed for 10 hours. A part (about 150 ml) of the reaction mixture was concentrated under reduced pressure. The residue was stirred with n-hexane (30 ml) at room temperature for 5 hours. Crystals produced were filtered and dried to yield racemic cis-1,3-dibenzyl-5-isopropoxycarbonyl-2-oxoimidazolidine-4-carboxylic acid (9.61 g). M.P., 108°-109° C.

Workup

  1. temperaturewas refluxed for 10 hours
  2. concentrationA part (about 150 ml) of the reaction mixture was concentrated under reduced pressure
  3. customCrystals produced
  4. filtrationwere filtered
  5. customdried

Sources & evidence

ORD record
ord-dbc375aef350427f88eab3186615112d
Source dataset
uspto-grants-1985_01
Patent number
US04496739

Reaction notes

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