Reacción #67358

Ecuación de reacción

water

sodium bicarbonate

(S)-6-amino-7-hydroxy-3,4-dihydro-1H-isoquinoline-2,3-dicarboxylic acid 2-isopropyl ester 3-methyl ester

2-Chloro-2-[4-(3,4-dichloro-benzyloxy)-phenyl]-acetyl chloride

→

(S)-3-[4-(3,4-Dichloro-benzyloxy)-phenyl]-2-oxo-1,2,3,5,7,8-hexahydro-4-oxa-1,6-diaza-anthracene-6,7-dicarboxylic acid 6-isopropyl ester 7-methyl ester

Disolventes

EtOAc

EtOAc

Condiciones de reacción

Tratamiento posterior

1. 1
   LavadoThe organic layer was washed with brine
2. 2
   Otrodried
3. 3
   Otroevaporated
4. 4
   workup.DISSOLUTIONThe residue was dissolved in 15 mL DMF
5. 5
   workup.ADDITIONpotassium carbonate (4.1 g) added
6. 6
   workup.STIRRINGThe mixture stirred at rt for 3 h
7. 7
   workup.ADDITIONwas poured onto water and EtOAc
8. 8
   LavadoThe organic was washed with 1N HCl
9. 9
   Otrodried
10. 10
    Otroevaporated
11. 11
    OtroThe residue was purified over silica (hexanes-EtOAc-2M ammonia in MeOH)

Procedimiento

(S)-6-amino-7-hydroxy-3,4-dihydro-1H-isoquinoline-2,3-dicarboxylic acid 2-isopropyl ester 3-methyl ester (1.8 g) was dissolved in 10 mL EtOAc, 20 mL water and 5.0 g sodium bicarbonate added. 2-Chloro-2-[4-(3,4-dichloro-benzyloxy)-phenyl]-acetyl chloride in 10 mL of EtOAc was added and the mixture stirred at rt for 1.5 h. The organic layer was washed with brine, dried and evaporated. The residue was dissolved in 15 mL DMF and potassium carbonate (4.1 g) added. The mixture stirred at rt for 3 h and was poured onto water and EtOAc. The organic was washed with 1N HCl, dried and evaporated. The residue was purified over silica (hexanes-EtOAc-2M ammonia in MeOH) to provide (S)-3-[4-(3,4-Dichloro-benzyloxy)-phenyl]-2-oxo-1,2,3,5,7,8-hexahydro-4-oxa-1,6-diaza-anthracene-6,7-dicarboxylic acid 6-isopropyl ester 7-methyl ester (2.0 g). LC-MS (m/z) 600.

Fuente