Methanol → Melevodopa hydrochloride

HRID 617775Notes

Reaction equation

HRID 617775 reaction equation
[O:1]=[C:2]([C@H:4]([CH2:6][C:7]1[CH:14]=[C:12]([OH:13])[C:10]([OH:11])=[CH:9][CH:8]=1)[NH2:5])[OH:3].S(Cl)([Cl:17])=O.[CH3:19]O>>[ClH:17].[CH3:19][O:1][C:2](=[O:3])[C@H:4]([CH2:6][C:7]1[CH:8]=[CH:9][C:10]([OH:11])=[C:12]([OH:13])[CH:14]=1)[NH2:5]

Participants

4

Reactant 3

HCID 887MethanolHCID 6047LevodopaHCID 24386Thionyl Chloride

Product 1

HCID 10131132Melevodopa hydrochloride

Procedure

A solution of 1.97 g (10 mmol) of L-DOPA 15 in 100 ml of MeOH at 0° C. was added 6.57 ml (90 mmol) of thionyl chloride via addition funnel. The mixture was stirred overnight while the temperature was slowly warmed to room temperature. The solvent was evaporated and the thick oil was treated with toluene (3×15 ml) and evaporated. The yield of white solid was 3.26 g (100%); NMR (DMSQ-d6) δ 2.90 (m, 2H), 3.38 (bs, 2H), 3.61 (s, 3H), 4.08 (m, 1H), 6.40 (d, 1H, J=7 Hz), 6.59 (s, 1H), 6.65(d, 2H, J=7 Hz), 8.59 (bs, 1H), 8.90 (d, 1H, J=10 Hz). MS: 212 m/z (M+H)+.

Workup

  1. additionvia addition funnel
  2. customThe solvent was evaporated
  3. additionthe thick oil was treated with toluene (3×15 ml)
  4. customevaporated

Sources & evidence

ORD record
ord-96eb6bde42034c87a9def152b9ced03f
Source dataset
uspto-grants-1999_09
Patent number
US05952328

Reaction notes

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