Reacción #213874

Ecuación de reacción

methyl ester

3-Carbomethoxymethyl-4-oxo-5-phthalimido-1,3-thiazine

tetrahydrofuran

hydrochloric acid

→

3-Carboxymethyl-4-oxo-5-phthalimido-1,3-thiazine

Disolventes

water

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe solution was cooled
2. 2
   workup.ADDITIONdiluted with 5 ml
3. 3
   Extracciónof water and then extracted four times with a total of 15 ml
4. 4
   SecadoThe organic phase was dried over sodium sulfate
5. 5
   Concentraciónconcentrated in vacuo
6. 6
   OtroThe resulting residue was triturated with dichloromethane and crystals
7. 7
   Otroformed
8. 8
   Lavadowhich were washed with dichloromethane
9. 9
   Otrodried
10. 10
    Otroto give 10.1 mg
11. 11
    ConcentraciónThe mother liquor on concentration in vacuo
12. 12
    Otroalso crystallized
13. 13
    Otroto give 13.3 mg

Procedimiento

A 24 mg. (0.07 mmole) sample of the methyl ester product obtained in Step A. above, in a solution of 1.5 ml. of tetrahydrofuran, 0.5 ml. of water, and 0.25 ml. of concentrated hydrochloric acid, was refluxed under nitrogen for 3.5 hrs. The solution was cooled and diluted with 5 ml. of water and then extracted four times with a total of 15 ml. of dichloromethane. The organic phase was dried over sodium sulfate and concentrated in vacuo. The resulting residue was triturated with dichloromethane and crystals formed, which were washed with dichloromethane and dried to give 10.1 mg. of product having a m.p. of 227°-228° C. The mother liquor on concentration in vacuo also crystallized to give 13.3 mg. of product.

Fuente