Water → HCID 729944, compound

HRID 1372786Notes

Reaction equation

HRID 1372786 reaction equation
[C:1]([OH:10])(=O)[C@H:2]([C@@H:4]([C:6](O)=[O:7])[OH:5])[OH:3].[CH2:11]([NH2:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.O>C1(C)C(C)=CC=CC=1>[CH2:11]([N:18]1[C:6](=[O:7])[C@@H:4]([OH:5])[C@H:2]([OH:3])[C:1]1=[O:10])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 962WaterHCID 7504BenzylamineHCID 439655D-Tartaric acid

Product 1

HCID 729944HCID 729944, compoundYield 84,635.797%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

In xylene (500 ml), D-tartaric acid (25.0 g, 0.17 mol) and benzylamine (19.6 g, 0.18 mmol) were heated under reflux for 18 hours by using a Dean-Stark water separator. After cooling, the reaction mixture was distilled under reduced pressure to remove the solvent, whereby 1-benzyl-(3S,4S)-dihydroxy-2,5-dioxopyrrolidine (33.7 g, 90%) was obtained as a brown solid.

Workup

  1. temperatureunder reflux for 18 hours
  2. temperatureAfter cooling
  3. distillationthe reaction mixture was distilled under reduced pressure
  4. customto remove the solvent

Sources & evidence

ORD record
ord-1eb2cd00b5fd4c80b06b7c3c0a6d6cf7
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Reaction notes

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