Reaktion #536366

ord-1de4fdd9eafd4a31850d4001408ac03a

Reaktionsgleichung

COC(N)=O
methyl carbamate
O=C(O)C(=O)CC[PH](=O)CO
2-oxo-4-(hydroxymethylphosphinyl)-butanoic acid
CC(=O)O
acetic acid
→
COC(=O)N/C(=C\C[PH](=O)CO)C(=O)O
objective compound
Ausbeute 71.9%
COC(=O)N/C(=C\C[PH](=O)CO)C(=O)O
(Z)-2-methoxycarbonylamino-4-(hydroxymethylphosphinyl)-2-butenoic acid
Ausbeute 71.9%

Edukte

COC(N)=O
methyl carbamate
O=C(O)C(=O)CC[PH](=O)CO
2-oxo-4-(hydroxymethylphosphinyl)-butanoic acid
CC(=O)O
acetic acid

Reagenzien

Cc1ccc(S(=O)(=O)O)cc1.O
p-toluenesulfonic acid monohydrate

Lösungsmittel

Cc1ccccc1
toluene

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    workup.DISSOLUTIONAfter being dissolved
  2. 2
    Temperaturby heating
  3. 3
    Temperaturthe solution was refluxed with vigorous stirring

Vorschrift

67.56 g of methyl carbamate, 2.97 g of p-toluenesulfonic acid monohydrate and 108.06 g of 2-oxo-4-(hydroxymethylphosphinyl)-butanoic acid were added to 160 mL of acetic acid to be suspended. After being dissolved by heating, 800 mL of toluene was added thereto and then the solution was refluxed with vigorous stirring. According to the same procedure as Example 1, 102.28 g of the objective compound was obtained (71.9% yield, Z:E=99.8:0.2).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08481779B2uspto-grants-2013_07