반응 #49998

반응 방정식

sulfuric acid

water

(3S,4S)-4-(1-(R)-hydroxymethylethyl)-3-(1-(R)-benzyloxycarbonyloxyethyl)-2-azetidinone

Jones reagent

→

(3S,4S)-4-(1-(R)-carboxyethyl)-3-(1-(R)-benzyloxycarbonyloxyethyl)-2-azetidinone

용매

acetone

반응 조건

후처리

1. 1
   기타The reaction mixture was quenched with isopropanol (0.5 ml) at 10°-20° C. for 15 minutes
2. 2
   workup.ADDITIONdiluted with ethyl acetate (122 ml)
3. 3
   세척washed with water (135 ml)
4. 4
   기타The aqueous layer was separated from the organic layer
5. 5
   추출extracted with ethyl acetate (61 ml)
6. 6
   추출extracted with 5% aqueous sodium bicarbonate solution (30 ml)
7. 7
   세척The extract was washed with dichloromethane (60 ml)
8. 8
   온도cooling
9. 9
   추출The acidic solution was extracted twice with dichloromethane (60 ml)
10. 10
    세척The extracts were washed with brine
11. 11
    건조dried over anhydrous sodium sulfate
12. 12
    여과After filtration
13. 13
    농축the filtrate was concentrated in vacuo

실험 절차

A solution of (3S,4S)-4-(1-(R)-hydroxymethylethyl)-3-(1-(R)-benzyloxycarbonyloxyethyl)-2-azetidinone (6.1 g) in acetone (60 ml) was treated with the Jones reagent, prepared from chromium trioxide (2.78 g), 98% sulfuric acid (4.4 g) and water (8.1 ml), at 10°-20° C. for 1 hour. The reaction mixture was quenched with isopropanol (0.5 ml) at 10°-20° C. for 15 minutes, diluted with ethyl acetate (122 ml) and washed with water (135 ml). The aqueous layer was separated from the organic layer and extracted with ethyl acetate (61 ml). The ethyl acetate extracts and the organic layer were combined together and extracted with 5% aqueous sodium bicarbonate solution (30 ml). The extract was washed with dichloromethane (60 ml) and acidified with 10% hydrochloric acid solution (20 ml) with ice-cooling. The acidic solution was extracted twice with dichloromethane (60 ml). The extracts were washed with brine and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated in vacuo to give (3S,4S)-4-(1-(R)-carboxyethyl)-3-(1-(R)-benzyloxycarbonyloxyethyl)-2-azetidinone.

출처