Methanol → (R)-Methyl 2-amino-3-(naphthalen-2-yl)propanoate

HRID 849833Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 849833
S(Cl)(Cl)=O.[CH:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7][C:6]=1[CH2:15][C@H:16]([C:18]([OH:20])=[O:19])[NH2:17].[CH3:21]O>>[CH3:21][O:19][C:18](=[O:20])[C@@H:16]([CH2:15][C:6]1[CH:7]=[CH:8][C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:5]=1)[NH2:17]

Komponenten

4

Edukt 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 2733661D-3-(2-Naphthyl)alanine

Produkt 1

HCID 7016520(R)-Methyl 2-amino-3-(naphthalen-2-yl)propanoate

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

Thionyl chloride (5 ml) was added dropwise over 15 min. to a suspension of (R)-3-(2-naphthyl)alanine (5.0 g) in methanol (50 ml) at 35° C. After addition the mixture was heated at 60° C. for 1 h, cooled and the solvent removed in vacuo. Water (75 ml) and ethyl acetate (125 ml) were added and pH was adjusted to 8.5 with sodium carbonate. The organic phase was separated and dried (magnesium sulfate) to afford 4.86 g of (R)-3-(2-naphthyl)alanine methyl ester.

Aufarbeitung

  1. additionAfter addition the mixture
  2. temperaturecooled
  3. customthe solvent removed in vacuo
  4. additionWater (75 ml) and ethyl acetate (125 ml) were added
  5. customThe organic phase was separated
  6. dry with materialdried (magnesium sulfate)

Quellen und Nachweise

ORD-Eintrag
ord-9fee042f5a194b0a99ca3fec5acf6ec1
Quelldatensatz
uspto-grants-2000_01
Patentnummer
US06013658

Notizen zur Reaktion

Wird geladen…