반응 #8269

반응 방정식

3-(4-(1-(2,2-Dimethyl-1,3-dioxolan-4(S)-ylcarbonyl)-1,2,5,6-tetrahydropyrid-4-yl)-3,5-difluorophenyl)-5(R)(N-(t-butoxycarbonyl)-3-methylisoxazol-5-ylaminomethyl)oxazolidin-2-one

trifluoroacetic acid

water

→

desired product

수율 58.5%

3-(4-(1-(2(S),3-Dihydroxypropanoyl)-1,2,5,6-tetrahydropyrid-4-yl)-3,5-difluorophenyl)-5(S)-(3-methylisoxazol-5-ylaminomethyl)oxazolidin-2-one

수율 58.5%

용매

dichloromethane

반응 조건

후처리

1. 1
   workup.STIRRINGstirring
2. 2
   workup.WAITcontinued for 1 hour
3. 3
   기타Solvent was removed
4. 4
   workup.DISSOLUTIONthe residue dissolved in methanol (20 ml)
5. 5
   workup.ADDITIONtreated with aqueous ammonia
6. 6
   기타solvent was removed
7. 7
   기타the residue chromatographed on a 10 g silica Mega Bond Elut® column
8. 8
   세척eluting with
9. 9
   온도a gradient increasing in polarity from 0 to 5% methanol in dichloromethane
10. 10
    기타evaporated

실험 절차

3-(4-(1-(2,2-Dimethyl-1,3-dioxolan-4(S)-ylcarbonyl)-1,2,5,6-tetrahydropyrid-4-yl)-3,5-difluorophenyl)-5(R)(N-(t-butoxycarbonyl)-3-methylisoxazol-5-ylaminomethyl)oxazolidin-2-one (400 mg, 0.65 mM) was dissolved in dichloromethane (6 ml) and treated with trifluoroacetic acid (6 ml) at 0°. After stirring for 30 minutes at ambient temperature, water (1.2 ml) was added, and stirring continued for 1 hour. Solvent was removed, the residue dissolved in methanol (20 ml), and treated with aqueous ammonia to bring the pH to 7–8; solvent was removed, and the residue chromatographed on a 10 g silica Mega Bond Elut® column, eluting with a gradient increasing in polarity from 0 to 5% methanol in dichloromethane. Relevant fractions were combined and evaporated to give the desired product (181 mg).

출처