Ethanol → Etilevodopa

HRID 260088Notes

Reaction equation

HRID 260088 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
40 °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. temperaturea cooled (2°-8° C.) solution of 30 ml
  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-048a27d93e4c4f6f8b946eff6e3590d8
Source dataset
uspto-grants-1996_06
Patent number
US05525631

Reaction notes

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