Reaktion #3154

ord-dba6f3dde0664944932faac3af102356

Reaktionsgleichung

CI
iodomethane
COC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)OCc1ccccc1
N-benzyloxycarbonyl-tyrosine methyl ester
O=C([O-])[O-].[K+].[K+]
potassium carbonate
→
COC(=O)[C@H](Cc1ccc(OC)cc1)NC(=O)OCc1ccccc1
N-Benzyloxycarbonyl-O-methyl-tyrosine methyl ester

Edukte

CI
iodomethane
COC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)OCc1ccccc1
N-benzyloxycarbonyl-tyrosine methyl ester
O=C([O-])[O-].[K+].[K+]
potassium carbonate

Reagenzien

Keine

Lösungsmittel

CN(C)C=O
DMF

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    EinengenThe solution is concentrated by evaporation
  2. 2
    workup.ADDITIONdispersed between ethyl acetate and water
  3. 3
    workup.ADDITIONthe organic phase is mixed with hexane
  4. 4
    Trocknenafter drying (Na2SO4)
  5. 5
    SonstigeThe title compound crystallizes out

Vorschrift

32.94 g (100 mmol) of N-benzyloxycarbonyl-tyrosine methyl ester is mixed in 200 ml of DMF with 27.64 g (200 mmol) of ground potassium carbonate. 15.6 g (110 mmol) of iodomethane is instilled in this suspension and stirred overnight at room temperature. The solution is concentrated by evaporation, dispersed between ethyl acetate and water, and the organic phase is mixed with hexane after drying (Na2SO4). The title compound crystallizes out.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05733522uspto-grants-1998_03