Diphenylphosphinic chloride → HCID 70510866, Verbindung

Temperatur

-20 °C

Diisopropylethylamine (0.90 ml.), then diphenylphosphinyl chloride (1.23 g.), were added to a solution of N-(tert-butyloxycarbonyl)-O-(tert-butyl)-N-methyl-L-tyrosine (1.76 g.) in tetrahydrofuran (15 ml.) maintained at -20° C., and the mixture was stirred for ten minutes. A solution of N-(3-phenylpropyl)-D-methioninamide hydrochloride (1.58 g.) and diisopropylethylamine (0.90 ml.) in tetrahydrofuran (10 ml.) was then added. The mixture was stirred for one half hour at -20°, one hour at 0° C. and overnight at room temperature, then filtered and stripped of solvent. A solution of the residue in ethyl acetate (100 ml.) was washed with water, aqueous citric acid, water again, aqueous sodium bicarbonate and water again, dried and stripped of solvent. Purification of the residue by high pressure liquid chromatography on silica gel (350 g.) using hexane-ethyl acetate (2:1) as the eluant afforded in fractions 6-7 (k'=8-14) [N-(tert-butyloxycarbonyl)-O-(tert-butyl)-N-methyl-L-tyrosyl]-N-(3-phenylpropyl)-D-methioninamide as a clear gum (2.1 g.).

1. stirringThe mixture was stirred for one half hour at -20°, one hour at 0° C. and overnight at room temperature
2. filtrationfiltered
3. washA solution of the residue in ethyl acetate (100 ml.) was washed with water, aqueous citric acid, water again
4. dry with materialaqueous sodium bicarbonate and water again, dried
5. customPurification of the residue by high pressure liquid chromatography on silica gel (350 g.)

ORD-Eintrag

ord-214dff10a3984679bf10cc884e0c0e85

Quelldatensatz

uspto-grants-1984_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US04454120