Reacción #57313

Ecuación de reacción

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

Rendimiento 92.0%

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

Rendimiento 92.0%

Disolventes

chloride

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwere added
2. 2
   OtroThey were reacted at room temperature for 1 hour
3. 3
   Extracciónextraction
4. 4
   LavadoOrganic layer was washed with brine
5. 5
   Secadodried over anhydrous MgSO4
6. 6
   Concentraciónconcentrated under reduced pressure
7. 7
   OtroThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1)

Procedimiento

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.

Fuente