4-Methylmorpholine → BOC-MePhe-NHCH2CH2CH2NMe2

N-t-Butyloxycarbonyl-N-methylphenylalanine (2.79 g) and NMM (1.01 g) were dissolved in dichloromethane (20 ml) and the stirred solution cooled to -20° IBCF (1.37 g) was then added and the mixture stirred for 5 minutes before the addition of NH2CH2CH2CH2NMe2 (1.02 g). The solution was stirred for 1 hour at -20° and then at room temperature for 12 hours. The mixture was evaporated, and the residue dissolved in ethyl acetate (50 ml) and an aqueous solution of sodium bicarbonate (saturated, 50 ml). The ethyl acetate layer was washed with aqueous sodium bicarbonate (saturated, 50 ml), water (2×50 ml) and 10% aqueous citric acid (2×50 ml). The citric acid extracts were combined, made basic with saturated sodium bicarbonate solution, and extracted with ethyl acetate (3×50 ml). The ethyl acetate extracts were combined, dried (Na2SO4) and evaporated to yield the title compound as an oil Rf1E 0.24, Rf3A 0.37.

1. temperaturethe stirred solution cooled to -20° IBCF (1.37 g)
2. additionwas then added
3. waitat room temperature for 12 hours
4. customThe mixture was evaporated
5. dissolutionthe residue dissolved in ethyl acetate (50 ml)
6. washThe ethyl acetate layer was washed with aqueous sodium bicarbonate (saturated, 50 ml), water (2×50 ml) and 10% aqueous citric acid (2×50 ml)
7. extractionextracted with ethyl acetate (3×50 ml)
8. dry with materialdried (Na2SO4)
9. customevaporated

ORD-Eintrag

ord-f00e84a52ab6457ab47b7b92b699c88c

Quelldatensatz

uspto-grants-1979_12

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US04178371