Reaktion #337634

Reaktionsgleichung

ClCO2iBu

4-benzyloxy-1-dimethylcarbamoyl-isoquinoline-3-carboxylic acid

NEt3

glycine benzyl ester hydrochloride

→

title compound

[(4-Benzyloxy-1-dimethylcarbamoyl-isoquinoline-3-carbonyl)-amino]-acetic acid benzyl ester

Lösungsmittel

CH2Cl2

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooled with an ice bath
2. 2
   workup.ADDITIONwas added
3. 3
   Sonstigewas removed
4. 4
   workup.STIRRINGStirring
5. 5
   Einengenthe mixture was concentrated in vacuo
6. 6
   workup.ADDITIONTo the residue was added water (10 ml) and a few drops of aqueous 6N HCl
7. 7
   ExtraktionThe mixture was extracted with EtOAc (15 ml)
8. 8
   TrocknenThe organic phase was dried over MgSO4
9. 9
   Einengenconcentrated in vacuo
10. 10
    Sonstigeto give a yellowish gum
11. 11
    SonstigePurification by flash column chromatography on silica gel

Vorschrift

To a mixture of 4-benzyloxy-1-dimethylcarbamoyl-isoquinoline-3-carboxylic acid (210 mg, 0.6 mmol), NEt3 (175 μl, 1.25 mmol), and CH2Cl2 (12 ml) cooled with an ice bath was added ClCO2iBu (83 μl, 0.63 mmol) with stirring. After stirring for 15 min glycine benzyl ester hydrochloride (127 mg, 0.63 mmol) was added and the mixture was stirred for another 15 min before the ice bath was removed. Stirring was then continued at ambient temperature for additional 1.5 h. Subsequently; the mixture was concentrated in vacuo. To the residue was added water (10 ml) and a few drops of aqueous 6N HCl. The mixture was extracted with EtOAc (15 ml). The organic phase was dried over MgSO4 and concentrated in vacuo to give a yellowish gum. Purification by flash column chromatography on silica gel using hexanes:EtOAc=7:3 as the eluent gave the title compound as a slightly yellowish gum (211 mg); MS-(+)-ion: M+1=498.1.

Quelle