Ethanol → Hydrochloric Acid

HRID 1397871Notes

Reaction equation

HRID 1397871 reaction equation
O=S(Cl)[Cl:3].[O:5]=[C:6]([C@H:8]([CH2:10][C:11]1[CH:18]=[C:16]([OH:17])[C:14]([OH:15])=[CH:13][CH:12]=1)[NH2:9])[OH:7].[CH3:19][CH2:20]O>>[NH2:9][CH:8]([CH2:10][C:11]1[CH:12]=[CH:13][C:14]([OH:15])=[C:16]([OH:17])[CH:18]=1)[C:6]([O:7][CH2:19][CH3:20])=[O:5].[ClH:3]

Participants

5

Reactant 3

HCID 702EthanolHCID 6047LevodopaHCID 24386Thionyl Chloride

Product 2

HCID 313Hydrochloric AcidYield 99%HCID 11790865HCID 11790865, compound

Conditions

Temperature
-5 °C

Procedure

To 30 mL of EtOH at −5° C. was added, with stirring, 0.37 mL of SOCl2 slowly. The clear colorless solution was cooled to −5° C. and 1 g of L-Dopa was added. After 5 min, the resulting solution was refluxed overnight. The solution was concentrated to afford 164 as HCl salt (1.30 g, 99%). 1H NMR (DMSO): δ 1.29 (t, 3H, J=7.4 Hz), 3.03 (m, 1H), 3.15 (m, 1H), 4.21 (m, 1H), 4.27 (m, 2H), 4.35 (sl, 3H), 6.60 (d, 1H, J=7.9 Hz), 6.74 (s, 1H), 6.82 (d, 1H, J=7.9 Hz), 8.63 (s, 2H).

Workup

  1. temperaturethe resulting solution was refluxed overnight
  2. concentrationThe solution was concentrated

Sources & evidence

ORD record
ord-099adfb875a14c5eaee8a90d80b3cdcf
Source dataset
uspto-grants-2014_12
Patent number
US08901295B2

Reaction notes

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