تفاعل #820502

معادلة التفاعل

TMSONH2

HOPO

crude acid 1b

3(S)-(4-Chloro-phenyl)-2(S)-ethyl-4-morpholin-4-yl-4-oxo-butyric acid

TMSONH2

→

3(S)-(4-Chloro-phenyl)-2(S)-ethyl-N-hydroxy-4-morpholin-4-yl-4-oxo-butyramide

المذيبات

dichloromethane

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGstirring
2. 2
   workup.WAITcontinued over night
3. 3
   ترشيحThe reaction mixture was filtered (solid
4. 4
   workup.ADDITIONdiluted with 20 ml of dichloromethane
5. 5
   استخلاصextracted twice with 2N-HCl and brine
6. 6
   تجفيفdried over anhydrous sodium sulfate
7. 7
   أخرىevaporated
8. 8
   أخرىThe crude solid (237 mg, 73%) was purified by preparative HPLC (methanol/water=1/1)

الإجراء التجريبي

The crude acid 1b (310 mg, 0.95 mmol) was dissolved in 5 ml of dichloromethane. HOPO (111 mg, 1 mmol) and MEI (0.159 ml, 1.14 mmol) were added successively. The mixture was stirred for 30 minutes, then TMSONH2 (0.233 ml, 1.9 mmol) was added. After one hour another portion of TMSONH2 (0.233 ml, 1.9 mmol) was added and stirring continued over night. The reaction mixture was filtered (solid contained mostly HOPO) diluted with 20 ml of dichloromethane and extracted twice with 2N-HCl and brine, dried over anhydrous sodium sulfate and evaporated. The crude solid (237 mg, 73%) was purified by preparative HPLC (methanol/water=1/1). Yield: 100 mg (31%).

المصدر