반응 #41877

반응 방정식

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

용매

EtOAc

EtOAc

반응 조건

후처리

1. 1
   세척The organic layer was washed with brine
2. 2
   기타dried
3. 3
   기타evaporated
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 r.t. for 3 h
7. 7
   workup.ADDITIONwas poured onto water and EtOAc
8. 8
   세척The organic was washed with 1N HCl
9. 9
   기타dried
10. 10
    기타evaporated
11. 11
    기타The residue was purified over silica (hexanes-EtOAc-2M ammonia in MeOH)

실험 절차

(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 r.t. 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.

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