Reaktion #557872

Reaktionsgleichung

compound

(3′S,4′R,7′S,8′S,8a′R)-6″-chloro-8′-(3-chloro-2-fluorophenyl)-4,4-dimethyl-3′,4′-diphenyl-3′,4′,8′,8a′-tetrahydro-1′H-dispiro[cyclohexane-1,6′-pyrrolo[2,1-c][1,4]oxazine-7′,3″-pyrrolo[2,3-b]pyridine]-1′,2″(1″H)-dione

sodium hydroxide

benzyloxycarbonyl chloride

hydrochloric acid

→

title compound

Ausbeute 37.0%

1,5-Anhydro-2-{[(benzyloxy)carbonyl]amino}-2,3,4-trideoxy-D-erythro-hexitol

Ausbeute 37.0%

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionfollowed by extraction with ethyl acetate
2. 2
   WaschenThe organic layer was washed with brine
3. 3
   Trocknendried over anhydrous magnesium sulfate
4. 4
   SonstigeThe solvent was evaporated under reduced pressure, diethyl ether and hexane
5. 5
   workup.ADDITIONwere added to the residue
6. 6
   Sonstigeobtained
7. 7
   Filtrationthe slurry was filtered
8. 8
   Sonstigedried

Vorschrift

The compound (3.5 g, 21.0 mmol) obtained in Step 1 above was dissolved in 5N aqueous sodium hydroxide solution (40 ml) and benzyloxycarbonyl chloride (3.3 ml, 23.0 mmol) was added dropwise at 0° C. After stirring at room temperature for 16 hours, the reaction mixture was rendered acidic by addition of 1N hydrochloric acid, followed by extraction with ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, diethyl ether and hexane were added to the residue obtained and then the slurry was filtered and dried to give 2.06 g (37%) of the title compound as a colorless solid.

Quelle