Hydrochloric Acid → HCID 19813279, compound

HRID 466981Notes

Reaction equation

HRID 466981 reaction equation
[S:1]1[CH:5]=[CH:4][S:3][C:2]1=[C:6]([C:13]([O:15]C(OCC)=O)=O)[C:7]([O:9][CH:10]([CH3:12])[CH3:11])=[O:8].[NH:21]1[CH2:28][CH2:27][CH2:26][C@H:22]1[C:23]([OH:25])=[O:24].Cl.[OH-].[Na+]>CN(C=O)C>[S:3]1[CH:4]=[CH:5][S:1][C:2]1=[C:6]([C:13]([N:21]1[CH2:28][CH2:27][CH2:26][CH:22]1[C:23]([OH:25])=[O:24])=[O:15])[C:7]([O:9][CH:10]([CH3:11])[CH3:12])=[O:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 145742L-ProlineHCID 19813261HCID 19813261, compound

Product 1

HCID 19813279HCID 19813279, compoundYield 91.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Isopropyl 2-(1,3-dithiol-2-ylidene)-2-(ethoxycarbonyloxy-carbonyl)acetate (13.2 g) and proline (4.6 g) was dissolved in DMF (60 ml). The mixture was stirred at room temperature for 24 hrs, thereto was added conc-HCl (20 ml) and stirred for a further 2 hrs. The reaction mixture was poured into ice water and basified to pH=12 with aqueous sodium hydroxide solution. The mixture was washed with methylene chloride and the aqueous layer was acidified to pH=2 with dil-HCl. The solid formed was filtered and recrystallized from ethyl acetate and n-hexane to obtain the pure product (12.5 g, 91%).

Workup

  1. stirringstirred for a further 2 hrs
  2. washThe mixture was washed with methylene chloride
  3. customThe solid formed
  4. filtrationwas filtered
  5. customrecrystallized from ethyl acetate and n-hexane

Sources & evidence

ORD record
ord-330a143342e7471abddb263920c7327c
Source dataset
uspto-grants-1992_10
Patent number
US05158950

Reaction notes

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