Sulfuric Acid → (3AS,6aR)-1,3-dibenzyltetrahydro-1H-furo(3,4-d)imidazole-2,4-dione

HRID 597597Notes

Reaction equation

HRID 597597 reaction equation
[CH2:1]([N:8]1[C@H:12]([CH2:13][OH:14])[C@H:11]([C:15](=[O:29])NC(C2C=CC3C(=CC=CC=3)C=2)C)[N:10]([CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:9]1=[O:37])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(=O)(=O)(O)O>O1CCOCC1>[CH2:1]([N:8]1[C@H:12]2[CH2:13][O:14][C:15](=[O:29])[C@H:11]2[N:10]([CH2:30][C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:9]1=[O:37])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 70637835HCID 70637835, compound

Product 1

HCID 119819(3AS,6aR)-1,3-dibenzyltetrahydro-1H-furo(3,4-d)imidazole-2,4-dione

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 4.0 g of the tetrahydroimidazol-2-one prepared in Example 11, 50 ml of dioxane and 30.0 g of 20 % sulfuric acid is stirred and refluxed for 2 hours. The mixture is concentrated to one third of the original volume in vacuo and diluted with 100 ml of water. The precipitate is collected by filtration to give 1.26 g (96.5 %) of optically active (+)-cis-1,3-dibenzyl-hexahydrofuro[3,4-d]imidazole-2,4-dione. M.P. 106 to 109° C. [α]D20 + 16.0° (C = 2 in CHCl3). The infrared spectrum of the sample is identical with that of the authentic sample.

Workup

  1. temperaturerefluxed for 2 hours
  2. concentrationThe mixture is concentrated to one third of the original volume in vacuo
  3. additiondiluted with 100 ml of water
  4. filtrationThe precipitate is collected by filtration

Sources & evidence

ORD record
ord-4e562eaab9404c9990e5d2f509810747
Source dataset
uspto-grants-1977_03
Patent number
US04014895

Reaction notes

Loading…