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

HRID 463734Notes

Reaction equation

HRID 463734 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-5d9b24a0b748450c9b680b80ca4094f8
Source dataset
uspto-grants-1985_10
Patent number
US04544635

Reaction notes

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