Trifluoroacetic acid → HCID 59215793, Verbindung

To a stirred solution of 1,1-dimethylethyl (3R)-3-{[[(1R)-1-(hydroxymethyl)-2-(methyloxy)-2-oxoethyl](phenylmethyl)amino]carbonyl}-4-morpholinecarboxylate (D103, 38.7 g, 0.092 moles) in 400 ml of DCM at room temperature, trifluoroacetic acid (68.3 ml, 0.92 moles) was slowly added. The resulting orange solution was stirred at room temperature overnight. It was then cooled by an ice-water bath and brought to pH=7-8 by adding sodium hydrogen carbonate (sat. solution, 250 ml and as solid). Phases were separated and the aqueous layer was extracted with DCM (3×300 ml). The combined organic extracts were dried (Na2SO4), concentrated under vacuum to afford a residue, which was dissolved in 270 ml of methanol and heated to 56-58° C. for 2 hours. The mixture was then allowed to cool down to room temperature and the solvent was removed under vacuum to afford a solid residue, which was treated with 100 ml of a mixture cyclohexane/EtOAc 8/2. The resulting suspension was stirred at room temperature for 30-40 minutes and then the solid was filtered off and collected to afford the title compound (1 8.7 g) as white solid.

1. temperatureIt was then cooled by an ice-water bath
2. customPhases were separated
3. extractionthe aqueous layer was extracted with DCM (3×300 ml)
4. dry with materialThe combined organic extracts were dried (Na2SO4)
5. concentrationconcentrated under vacuum
6. customto afford a residue, which
7. temperatureheated to 56-58° C. for 2 hours
8. temperatureto cool down to room temperature
9. customthe solvent was removed under vacuum
10. customto afford a solid residue, which
11. stirringThe resulting suspension was stirred at room temperature for 30-40 minutes
12. filtrationthe solid was filtered off
13. customcollected

ORD-Eintrag

ord-9fd175a404c74f588df5c9340cfbae47

Quelldatensatz

uspto-grants-2010_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07683056B2