Methanol → HCID 69331780, compound

HRID 1765987Notes

Reaction equation

HRID 1765987 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:5]=[C:6]([CH:13]=[CH:14][C:15]=1[CH3:16])[CH2:7][C@H:8]([C:10]([OH:12])=[O:11])[NH2:9].S(Cl)([Cl:19])=O.[CH3:21]O>>[ClH:19].[CH3:21][O:11][C:10](=[O:12])[C@@H:8]([CH2:7][C:6]1[CH:13]=[CH:14][C:15]([CH3:16])=[C:4]([O:3][CH3:2])[CH:5]=1)[NH2:9]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl Chloride2×HCID 69331765HCID 69331765, compound

Product 1

HCID 69331780HCID 69331780, compound

Conditions

Temperature
45 °C

Procedure

To a solution of 3-methoxy-4-methyl-D-phenylalanine hydrochloride (1.75 g) in methanol (8 ml) was added dropwise thionyl chloride (0.7 ml) at room temperature over 10 minutes. The total mixture was stirred at 40 to 50° C. for 2 hours and thionyl chloride (0.7 ml) was added further to the mixture. The total mixture was stirred for further 1 hour and the solvent was evaporated under reduced pressure. The produced solid substance was triturated with diisopropyl ether and collected by filtration to give 3-methoxy-4-methyl-D-phenylalanine methyl ester hydrochloride (1.70 g) in the form of colorless crystals.

Workup

  1. stirringThe total mixture was stirred for further 1 hour
  2. customthe solvent was evaporated under reduced pressure
  3. customThe produced solid substance was triturated with diisopropyl ether
  4. filtrationcollected by filtration

Sources & evidence

ORD record
ord-09257fd457f64b94b1667fb261961a24
Source dataset
uspto-grants-2007_06
Patent number
US07229992B2

Reaction notes

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