Reaktion #8263

Reaktionsgleichung

3-(4-(3(S)-Aminopyrrolidin-1-yl)-3-fluorophenyl)-5(R)-(N-(2,2,2-trichloroethyl-oxycarbonyl)isoxazol-3-ylaminomethyl)oxazolidin-2-one hydrochloride salt

2,2-dimethyl-1,3-dioxolan-4(S)-ylcarbonyl chloride

→

desired product

Ausbeute 143.5%

3-(4-(3(S)-(2(S),3-Dihydroxypropanoyl)pyrrolidin-1-yl)-3-fluorophenyl)-5(S)-(isoxazol-3-ylaminomethyl)oxazolidin-2-one

Ausbeute 143.5%

Lösungsmittel

pyridine

dichloromethane

ethyl acetate

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe organic layer separated
2. 2
   Waschenwashed with aqueous sodium bicarbonate (10 ml) and brine (10 ml)
3. 3
   Sonstigeevaporated
4. 4
   Sonstigeazeotroped with toluene (20 ml)
5. 5
   SonstigeThe residue was purified by chromatography on a 10 g silica Mega Bond Elut® column
6. 6
   Wascheneluting with
7. 7
   Temperatura gradient increasing in polarity from 0 to 100% ethyl acetate in dichloromethane
8. 8
   Sonstigeevaporated

Vorschrift

3-(4-(3(S)-Aminopyrrolidin-1-yl)-3-fluorophenyl)-5(R)-(N-(2,2,2-trichloroethyl-oxycarbonyl)isoxazol-3-ylaminomethyl)oxazolidin-2-one hydrochloride salt (400 mg, 0.698 mM) in pyridine (5 ml) was treated dropwise with a solution of 2,2-dimethyl-1,3-dioxolan-4(S)-ylcarbonyl chloride (200 mg, 1.2 mM) in dichloromethane (2 ml), and the mixture stirred 3 hours at ambient temperature. The mixture was diluted with ethyl acetate (15 ml) and water (15 ml), the organic layer separated, washed with aqueous sodium bicarbonate (10 ml) and brine (10 ml), and evaporated, then azeotroped with toluene (20 ml). The residue was purified by chromatography on a 10 g silica Mega Bond Elut® column, eluting with a gradient increasing in polarity from 0 to 100% ethyl acetate in dichloromethane. Relevant fractions were combined and evaporated to give the desired product (435 mg).

Quelle