Reacción #536367

Ecuación de reacción

methyl carbamate

2-oxo-4-(hydroxymethylphosphinyl)-butanoic acid

acetic acid

→

objective compound

Rendimiento 56.8%

(Z)-2-methoxycarbonylamino-4-(hydroxymethylphosphinyl)-2-butenoic acid

Rendimiento 56.8%

Disolventes

toluene

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.DISSOLUTIONAfter being dissolved
2. 2
   Temperaturaby heating
3. 3
   Temperaturathe solution was refluxed with vigorous stirring
4. 4
   Otrowas from 106 to 108 deg. C
5. 5
   OtroSix hours
6. 6
   FiltraciónThe deposited precipitate was filtered
7. 7
   Lavadothe filtrate was washed with acetic acid
8. 8
   LavadoAfter being washed with acetone
9. 9
   Otrodried for 5 hours from 40 to 50 deg. C

Procedimiento

16.673 g of methyl carbamate, 0.549 g of p-toluenesulfonic acid monohydrate, and 20.000 g of 2-oxo-4-(hydroxymethylphosphinyl)-butanoic acid were added to 56 mL of acetic acid to be suspended. After being dissolved by heating, 112 mL of toluene was added thereto and then the solution was refluxed with vigorous stirring. The internal temperature of the reaction solution was from 106 to 108 deg. C. Six hours later, dissipation of almost all the raw materials was confirmed by HPLC measurement. At this point, the area ratio of Z form to E form was 81:19. The deposited precipitate was filtered and then the filtrate was washed with acetic acid. After being washed with acetone, dried for 5 hours from 40 to 50 deg. C. under a reduced pressure, 14.966 g of the objective compound was obtained (56.8% yield, Z:E=99.7:0.3).

Fuente