Dimethylformamide → HCID 22099474, compound

Triethylamine (13.3 ml) was added dropwise to a mixture of 5 g of bis(2-hydroxyethyl)amine, 14.3 g of tert-butyl-dimethylsilyl chloride and 100 ml of dimethylformamide (DMF). A catalytic amount of 4-dimethylaminopyridine was added to the mixture and the resulting mixture was stirred for 5 hours. Then, the mixture was diluted with ethyl acetate. The diluted mixture was washed and dried, and the solvent was removed under reduced pressure. To the obtained residue were added 10.6 g of 3-(N-benzyloxycarbonylamino)-propionic acid, 7.1 g of 1-hydroxybenzotriazole and 100 ml of DMF, and under ice-cooling, 10.8 g of 1,3-dicyclohexylcarbodiimide (DCC) was added to the mixture. The resulting mixture was stirred at room temperature overnight. The mixture was diluted with ethyl acetate, and insoluble materials were removed from the mixture by filtration. The filtrate was washed and dried, and the solvent was removed under reduced pressure. The residue was applied to silica gel column chromatography (solvent; hexane:ethyl acetate=4:1). The condensed eluate was dissolved in 200 ml of methanol, and 1 g of 10% palladium-carbon (Pd-C) was added to the solution. The mixture was subjected to catalytic reduction at normal temperature under normal pressure for 0.5 hour. The catalyst was filtered off, and the filtrate was condensed to give 11.4 g of {2-[bis(2-tert-butyldimethylsilyloxyethyl)amino]carbonylethyl}amine (yield: 59%) as a colorless oily product.

1. washThe diluted mixture was washed
2. customdried
3. customthe solvent was removed under reduced pressure
4. additionTo the obtained residue were added 10.6 g of 3-(N-benzyloxycarbonylamino)-propionic acid, 7.1 g of 1-hydroxybenzotriazole and 100 ml of DMF
5. temperatureunder ice-cooling
6. addition10.8 g of 1,3-dicyclohexylcarbodiimide (DCC) was added to the mixture
7. stirringThe resulting mixture was stirred at room temperature overnight
8. additionThe mixture was diluted with ethyl acetate, and insoluble materials
9. customwere removed from the mixture by filtration
10. washThe filtrate was washed
11. customdried
12. customthe solvent was removed under reduced pressure
13. dissolutionThe condensed eluate was dissolved in 200 ml of methanol
14. addition1 g of 10% palladium-carbon (Pd-C) was added to the solution
15. waitThe mixture was subjected to catalytic reduction at normal temperature under normal pressure for 0.5 hour
16. filtrationThe catalyst was filtered off
17. customcondensed

ORD record

ord-566ff4aae71048c58b2c1acd641a2c26

Source dataset

uspto-grants-1998_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05849732