Chloromethyl Methyl Ether → 3-(4-Benzyloxy-2-methoxymethoxyphenyl)propionamide

To a stirred suspension of 5.64 g of 60% sodium hydride in oil in 628 mL of N,N-dimethylformamide was added 34.8 g of 3-(4-benzyloxy-2-hydroxyphenyl)propionamide under ice-cooling, and the mixture was stirred at 50° C. for 40 minutes. To the reaction mixture was added 12.39 g of chloromethyl methyl ether under ice-cooling, and the mixture was stirred at room temperature for 15 hours. After the reaction mixture was concentrated under reduced pressure to remove the solvent, the residue was poured into a mixture of 500 mL of ethyl acetate, 100 mL of toluene, and 200 mL of water. The organic layer was separated, washed with water, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure to give a colorless solid. The solid was triturated in ethyl acetate-diisopropyl ether to collect by filtration of 35.3 g of 3-(4-benzyloxy-2-methoxymethoxy-phenyl)propionamide as a colorless solid.

1. temperaturecooling
2. temperaturecooling
3. stirringthe mixture was stirred at room temperature for 15 hours
4. concentrationAfter the reaction mixture was concentrated under reduced pressure
5. customto remove the solvent
6. additionthe residue was poured into a mixture of 500 mL of ethyl acetate, 100 mL of toluene, and 200 mL of water
7. customThe organic layer was separated
8. washwashed with water
9. dry with materialdried over anhydrous magnesium sulfate
10. filtrationfiltered
11. concentrationThe filtrate was concentrated under reduced pressure
12. customto give a colorless solid
13. customThe solid was triturated in ethyl acetate-diisopropyl ether
14. filtrationto collect by filtration of 35.3 g of 3-(4-benzyloxy-2-methoxymethoxy-phenyl)propionamide as a colorless solid

ORD-Eintrag

ord-782db45584c34ef58e32a8df65fa517f

Quelldatensatz

uspto-grants-2007_04

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07208524B2