تفاعل #49998

معادلة التفاعل

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

المذيبات

acetone

ظروف التفاعل

المعالجة

1. 1
   أخرىThe 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
   غسيلwashed with water (135 ml)
4. 4
   أخرىThe aqueous layer was separated from the organic layer
5. 5
   استخلاصextracted with ethyl acetate (61 ml)
6. 6
   استخلاصextracted with 5% aqueous sodium bicarbonate solution (30 ml)
7. 7
   غسيلThe extract was washed with dichloromethane (60 ml)
8. 8
   درجة الحرارةcooling
9. 9
   استخلاصThe acidic solution was extracted twice with dichloromethane (60 ml)
10. 10
    غسيلThe extracts were washed with brine
11. 11
    تجفيفdried over anhydrous sodium sulfate
12. 12
    ترشيحAfter filtration
13. 13
    تركيزthe filtrate was concentrated in vacuo

الإجراء التجريبي

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.

المصدر