Ethanol → Etilevodopa

HRID 975132Notes

Reaction equation

HRID 975132 reaction equation
[CH:1]1[C:6]([CH2:7][C@H:8]([NH2:12])[C:9]([OH:11])=[O:10])=[CH:5][C:4]([OH:13])=[C:3]([OH:14])[CH:2]=1.S(Cl)(Cl)=O.[CH2:19](O)[CH3:20]>>[CH3:19][CH2:20][O:10][C:9]([C@@H:8]([NH2:12])[CH2:7][C:6]1[CH:1]=[CH:2][C:3]([OH:14])=[C:4]([OH:13])[CH:5]=1)=[O:11]

Participants

4

Reactant 3

HCID 702EthanolHCID 6047LevodopaHCID 24386Thionyl Chloride

Product 1

HCID 170345Etilevodopa

Conditions

Temperature
5 °C

Procedure

Levodopa (50 g.) was added in portions to a cooled (2-8° C.) solution of 30 ml. thionyl chloride in 250 ml. absolute ethanol. The resulting mixture was heated to 40° C. for 16 hours and then the volatiles were removed in vacuo. The residue was dissolved in 50 ml. of water and diluted with a solution of 20 g. of sodium bicarbonate, 26 g. of sodium sulfate and 50 mg. of ascorbic acid in 400 ml. of water. The pH of the resulting solution was carefully adjusted to pH 7 with 10% aqueous sodium hydroxide and it was extracted with deaerated ethyl acetate containing 0.01% BHT.

Workup

  1. temperatureThe resulting mixture was heated to 40° C. for 16 hours
  2. customthe volatiles were removed in vacuo
  3. dissolutionThe residue was dissolved in 50 ml
  4. additionof water and diluted with a solution of 20 g
  5. extractionwas extracted with deaerated ethyl acetate containing 0.01% BHT

Sources & evidence

ORD record
ord-f2d859bf08b343df8c61f90e49be1238
Source dataset
uspto-grants-1997_03
Patent number
US05607969

Reaction notes

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