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

HRID 1903366Notes

Reaction equation

HRID 1903366 reaction equation
[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]

Participants

4

Reactant 3

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

Product 1

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

Conditions

Temperature
-10 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-1268c11a6ee5464fb98f48f1072a3221
Source dataset
uspto-grants-1984_03
Patent number
US04435571

Reaction notes

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