تفاعل #8263

معادلة التفاعل

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

المردود 143.5%

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

المردود 143.5%

المذيبات

pyridine

dichloromethane

ethyl acetate

water

ظروف التفاعل

المعالجة

1. 1
   أخرىthe organic layer separated
2. 2
   غسيلwashed with aqueous sodium bicarbonate (10 ml) and brine (10 ml)
3. 3
   أخرىevaporated
4. 4
   أخرىazeotroped with toluene (20 ml)
5. 5
   أخرىThe residue was purified by chromatography on a 10 g silica Mega Bond Elut® column
6. 6
   غسيلeluting with
7. 7
   درجة الحرارةa gradient increasing in polarity from 0 to 100% ethyl acetate in dichloromethane
8. 8
   أخرىevaporated

الإجراء التجريبي

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).

المصدر