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

HRID 1701024Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1701024
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-84eb9e3bf8a5469d9bd6840d98f1248b
Quelldatensatz
uspto-grants-2002_02
Patentnummer
US06350767B1

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