Réaction #57313

Équation de réaction

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

Rendement 92.0%

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

Rendement 92.0%

Solvants

chloride

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONwere added
2. 2
   AutreThey were reacted at room temperature for 1 hour
3. 3
   Extractionextraction
4. 4
   LavageOrganic layer was washed with brine
5. 5
   Séchagedried over anhydrous MgSO4
6. 6
   Concentrationconcentrated under reduced pressure
7. 7
   AutreThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1)

Mode opératoire

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.

Source