Reacción #437793

Ecuación de reacción

product

N-(2-formyl-4-methoxyphenyl)formamide

L-glutamine

sodium borohydride

→

4-carbamoyl-2-(6-methoxy-4H-quinazolin-3-yl)butanoic acid

Disolventes

sodium hydroxide

methanol

methanol

sodium hydroxide

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturathe mixture was cooled to 0° C.
2. 2
   workup.STIRRINGThe mixture was stirred for 12 hours at 0° C.
3. 3
   workup.STIRRINGstirred for a further 4 hours at 20° C
4. 4
   workup.DISTILLATIONthe methanol was distilled off
5. 5
   LavadoThe aqueous residue was washed twice with 15 ml of diethyl ether each time
6. 6
   Concentraciónconcentrated by evaporation in vacuo
7. 7
   Filtraciónfreed from insoluble constituents by filtration
8. 8
   OtroThe residue obtained
9. 9
   Otroby evaporating the filtrate in vacuo
10. 10
    Otroas described in stage 5, without purification

Procedimiento

A solution of 0.79 g of the product from stage 3 in 30 ml of methanol was added to a solution of 0.58 g of L-glutamine in 10 ml of methanol and 2 ml of 2N sodium hydroxide solution. After stirring for 1 hour at 20° C., the mixture was cooled to 0° C. and 0.103 g of sodium borohydride was added in portions within 30 minutes. The mixture was stirred for 12 hours at 0° C., then adjusted to pH 2 to 3, and stirred for a further 4 hours at 20° C. After neutralizing the solution with sodium hydroxide, the methanol was distilled off. The aqueous residue was washed twice with 15 ml of diethyl ether each time, and then concentrated by evaporation in vacuo. The residue was taken up in 25 ml of methanol and freed from insoluble constituents by filtration. The residue obtained by evaporating the filtrate in vacuo was directly reacted further as described in stage 5, without purification.

Fuente