반응 #49995

반응 방정식

(3S,4S)-4-(1-hydroxymethylethenyl)-3-(1-(R)-benzyloxycarbonyloxyethyl)-1-di(p-anisyl)methyl-2-azetidinone

imidazole

t-butyldimethylchlorosilane

→

(3S,4S)-4-(1-t-butyldimethylsilyloxymethylethenyl)-3-(1-(R)-benzyloxycarbonyloxyethyl)-1-di(p-anisyl)methyl-2-azetidinone

용매

water

ethyl acetate

dimethylformamide

반응 조건

후처리

1. 1
   추출The aqueous layer was extracted with ethyl acetate (150 ml)
2. 2
   세척The combined extracts were washed successively with 5% hydrochloric acid solution (80 ml×2) and brine (80 ml)
3. 3
   건조dried over anhydrous sodium sulfate
4. 4
   여과After filtration
5. 5
   농축the filtrate was concentrated in vacuo
6. 6
   기타the concentrate was crystallized from isopropanol

실험 절차

A solution of (3S,4S)-4-(1-hydroxymethylethenyl)-3-(1-(R)-benzyloxycarbonyloxyethyl)-1-di(p-anisyl)methyl-2-azetidinone (20 g) and imidazole (5.6 g) in dry dimethylformamide (45 ml) was treated with t-butyldimethylchlorosilane (6.77 g) at room temperature for 2 hours. The reaction mixture was diluted with cold water (200 ml) and ethyl acetate (150 ml). The aqueous layer was extracted with ethyl acetate (150 ml). The combined extracts were washed successively with 5% hydrochloric acid solution (80 ml×2) and brine (80 ml), and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated in vacuo, and the concentrate was crystallized from isopropanol to give crystals of (3S,4S)-4-(1-t-butyldimethylsilyloxymethylethenyl)-3-(1-(R)-benzyloxycarbonyloxyethyl)-1-di(p-anisyl)methyl-2-azetidinone. m.p., 90°-92° C.

출처