반응 #57313

반응 방정식

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

수율 92.0%

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

수율 92.0%

용매

chloride

반응 조건

후처리

1. 1
   workup.ADDITIONwere added
2. 2
   기타They were reacted at room temperature for 1 hour
3. 3
   추출extraction
4. 4
   세척Organic layer was washed with brine
5. 5
   건조dried over anhydrous MgSO4
6. 6
   농축concentrated under reduced pressure
7. 7
   기타The residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1)

실험 절차

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.

출처