Formic Acid → hydroxy [(3S)-3-phenyl-1-({[4-(4-ethynylphenyl)piperazin-1-yl]sulfonyl}methyl)butyl]formamide

온도

0 °C

To formic acid (3.75 mL, 98 mmol) at 0° C. was added acetic anhydride (750 μL, 7.8 mmol) and the mixture was stirred at 0° C. for 10 minutes. This was added to a solution of 1-{[(4S)-2-(hydroxyamino)-4-phenylpentyl]sulfonyl}-4-[4-(trimethylsilylethynyl)phenyl]piperazine (720 mg, 94 wt %, 1.35 mmol) in CH2Cl2 (5 mL) cooled to 0° C. The reaction was brought quickly to RT and stirred for 20 minutes. Volatiles were then removed in vacuo, and the residue azeotroped with toluene (3×5 mL). The residue was then dissolved in MeOH (10 mL) and heated to 40° C. for two hours. The solution was then cooled to RT and concentrated in vacuo. The residue was then purified by flash chromatography (silica gel, 40–85% EtOAc in iHexane) and evaporated in vacuo. The solid was dissolved in ether/CH2Cl2 and the insoluble contaminant removed by filtration to give the title compound as a pink foam (90 mg, 0.171 mmol, 15%).

1. temperaturecooled to 0° C
2. customwas brought quickly to RT
3. stirringstirred for 20 minutes
4. customVolatiles were then removed in vacuo
5. customthe residue azeotroped with toluene (3×5 mL)
6. dissolutionThe residue was then dissolved in MeOH (10 mL)
7. temperatureheated to 40° C. for two hours
8. temperatureThe solution was then cooled to RT
9. concentrationconcentrated in vacuo
10. customThe residue was then purified by flash chromatography (silica gel, 40–85% EtOAc in iHexane)
11. customevaporated in vacuo
12. dissolutionThe solid was dissolved in ether/CH2Cl2
13. customthe insoluble contaminant removed by filtration

ORD 기록

ord-5ba62ed97fbf4c758f8b559ddadac662

출처 데이터셋

uspto-grants-2006_12

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US07153857B2