L-Proline → HCID 14127455, compound

HRID 648920Notes

Reaction equation

HRID 648920 reaction equation
[NH:1]1[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=[O:4].[Cl:9]([O-:13])(=[O:12])(=[O:11])=[O:10].CS[C:16]1[S:20][CH:19]=[CH:18][S+:17]=1>O1CCCC1>[Cl:9]([O-:13])(=[O:12])(=[O:11])=[O:10].[S:17]1[CH:18]=[CH:19][S:20][C:16]1=[N+:1]1[CH2:8][CH2:7][CH2:6][CH:2]1[C:3]([OH:5])=[O:4]

Participants

4

Reactant 2

HCID 145742L-ProlineHCID 230390092-Methylthio-1,3-dithiolium perchlorate

Product 1

HCID 14127455HCID 14127455, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 80 ml of tetrahydrofuran, 1.0 g of proline was suspended, and 2.0 g of 2-methylthio-1,3-dithiolium perchlorate was gradually added thereto under stirring at room temperature. The mixture was stirred at room temperature for 1 hour, and the solvent was distilled off under reduced pressure. The residue was dissolved in a mixture comprising 50 ml of water and 50 ml of ethyl acetate. The aqueous layer was separated and the solvent was distilled off under reduced pressure, whereby 1.6 g (yield: 63%) of 1-(1,3-dithiol-2-ylidene)-2-carboxypyrrolidinium perchlorate (Compound No. 43) was obtained as yellow oily residue.

Workup

  1. stirringThe mixture was stirred at room temperature for 1 hour
  2. distillationthe solvent was distilled off under reduced pressure
  3. dissolutionThe residue was dissolved in a mixture comprising 50 ml of water and 50 ml of ethyl acetate
  4. customThe aqueous layer was separated
  5. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-15f6227eeafd4a87b8926fbd47d58abe
Source dataset
uspto-grants-1988_04
Patent number
US04737494

Reaction notes

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