Reaktion #337631

Reaktionsgleichung

glycine benzyl ester hydrochloride

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

NEt3

ClCO2iBu

→

title compound

Ausbeute 81.0%

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

Ausbeute 81.0%

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
   EinengenSubsequently the 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-methoxymethyl-isoquinoline-3-carboxylic acid (120 mg, 0.37 mmol), NEt3 (109 μl, 0.78 mmol), and CH2Cl2 (7 ml) cooled with an ice bath was added ClCO2iBu (52 μl, 0.39 mmol) with stirring. After stirring for 15 min glycine benzyl ester hydrochloride (79 mg, 0.39 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 yellow oil (141 mg); MS-(+)-ion: M+1=471.1.

Quelle