Methanol → Methyl (2S)-2-amino-3-(4-fluorophenyl)propanoate

HRID 1980040Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1980040
[F:1][C:2]1[CH:13]=[CH:12][C:5]([CH2:6][C@@H:7]([C:9]([OH:11])=[O:10])[NH2:8])=[CH:4][CH:3]=1.S(Cl)(Cl)=O.[CH3:18]O>>[CH3:18][O:10][C:9](=[O:11])[C@H:7]([CH2:6][C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:13][CH:12]=1)[NH2:8]

Komponenten

4

Edukt 3

HCID 887Methanol2×HCID 24386Thionyl ChlorideHCID 7163124-fluoro-L-phenylalanine

Produkt 1

HCID 7018988Methyl (2S)-2-amino-3-(4-fluorophenyl)propanoate

Reaktionsbedingungen

Temperatur
-10 °C

Versuchsvorschrift

1.8 g (10 mmole) of 4-fluorophenylalanine is suspended in 3.0 ml of methanol and cooled to -10° C. under nitrogen and 0.81 ml of thionylchloride added dropwise, keeping the temperature at or below -2° C., and stirred for 1 hour at -5° C. to -10° C. About 10 ml of methanol was added and the solution stirred at room temperature overnight. The solution was concentrated in vacuo and the residue triturated with dry ether and filtered to give the hydrochloride salt of 4-fluorophenylalanine methyl ester, m.p. 177.5° to 178° C. The ester hydrochloride is substituted for L-phenylalanine methyl ester hydrochloride in the procedure of Example 6a to yield 6b.

Aufarbeitung

  1. custombelow -2° C.
  2. stirringthe solution stirred at room temperature overnight
  3. concentrationThe solution was concentrated in vacuo
  4. customthe residue triturated with dry ether
  5. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-3c88278928b543c8a333f95495170d8d
Quelldatensatz
uspto-grants-1984_11
Patentnummer
US04483988

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