Methanol → Methyl (2R)-amino(4-hydroxyphenyl)acetate--hydrogen chloride (1/1)

HRID 2236150

Reaktionsgleichung

Reaktionsgleichung von HRID 2236150
[CH:1]1[C:6]([C@@H:7]([NH2:11])[C:8]([OH:10])=[O:9])=[CH:5][CH:4]=[C:3]([OH:12])[CH:2]=1.S(Cl)([Cl:15])=O.[CH3:17]O>>[CH3:17][O:9][C:8]([C@H:7]([NH2:11])[C:6]1[CH:5]=[CH:4][C:3]([OH:12])=[CH:2][CH:1]=1)=[O:10].[ClH:15]

Komponenten

4

Edukt 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 89853D-p-hydroxyphenylglycine

Produkt 1

HCID 13215089Methyl (2R)-amino(4-hydroxyphenyl)acetate--hydrogen chloride (1/1)Ausbeute 95,3 %

Versuchsvorschrift

D-4-Hydroxyphenylglycine 11 (10.1 g, 60.4 mmol) was suspended in methanol (100 ml), and thionyl chloride (5.2 ml, 72.5 mmol) was added dropwise thereto at 50° C. over 0.5 hrs. After further keeping at 50° C. for 3 hrs, the solvent was distilled off under reduced pressure, and toluene and ethyl acetate were added to the residue. A resulting solid was collected by filtration and dried in vacuo to give D-4-hydroxyphenylglycine methyl ester hydrochloride 12 (12.5 g, yield 95.3%).

Aufarbeitung

  1. waitAfter further keeping at 50° C. for 3 hrs
  2. distillationthe solvent was distilled off under reduced pressure, and toluene and ethyl acetate
  3. additionwere added to the residue
  4. filtrationA resulting solid was collected by filtration
  5. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-a78cc828010e4deea20a42f3c8047c30
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07714157B2

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