Reaktion #57313

Reaktionsgleichung

NaHCO3

compound

(2R,3R,4S)-6-amino-3,4-dihydro-3-hydroxy-2-dimethoxymethyl-2-methyl-4-(2-thioxobenzoxazol-3-yl)-2H-1-benzopyran

triethylamine

→

target compound

Ausbeute 92.0%

(2R,3R,4S)-6-benzoylamino-3,4-dihydro-3-hydroxy-2-dimethoxymethyl-2-methyl-4-(2-thioxobenzoxazol-3-yl)-2H-1-benzopyran

Ausbeute 92.0%

Lösungsmittel

chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwere added
2. 2
   SonstigeThey were reacted at room temperature for 1 hour
3. 3
   Extraktionextraction
4. 4
   WaschenOrganic layer was washed with brine
5. 5
   Trocknendried over anhydrous MgSO4
6. 6
   Einengenconcentrated under reduced pressure
7. 7
   SonstigeThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1)

Vorschrift

80 mg (0.20 mmol) of the compound obtained in Example 17 was dissolved in 1 ml of tetrahydropurane, to which 23 μl (0.20 mmol) of benzoil chloride and 42 μl (0.30 mmol) of triethylamine were added. They were reacted at room temperature for 1 hour. Then, 10 ml of saturated NaHCO3 solution was added and extraction was performed with 30 ml of ethyl acetate. Organic layer was washed with brine and dried over anhydrous MgSO4, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1), to give 93 mg (yield: 92%) of the target compound.

Quelle