反応 #44005

反応方程式

diazomethane

compound 60

2-(4-chloro-N-(pent-1-yn-3-yl)phenylsulfonamido)-butanoic acid

triethylamine

isobutyl chloroformate

→

4-chloro-N-(1-diazo-2-oxopentan-3-yl)-N-(pent-1-yn-3-yl)benzenesulfonamide

溶媒

HOAc

Et2O

反応条件

後処理

1. 1
   workup.STIRRINGstirred there for 5 hours
2. 2
   その他to destroy the excess diazomethane
3. 3
   抽出the solution was extracted with EtOAc
4. 4
   洗浄The organic phase was washed with sat NaHCO3, water, brine
5. 5
   乾燥dried (MgSO4)

実験手順

To a solution of the compound 60 (498 mg, 1.45 mmol) in 7.5 mL of Et2O were added sequentially 0.24 mL of triethylamine (1.2 eq), 0.23 mL of isobutyl chloroformate (1.2 eq) at −30° C. After being stirred at −30° C. for 15 min, diazomethane (prepared by mixing MNNG and KOH in diethyl ether) (excess) was added to the above mixture at 0° C. and stirred there for 5 hours. Glacial HOAc (1.5 mL) was added to destroy the excess diazomethane and the solution was extracted with EtOAc. The organic phase was washed with sat NaHCO3, water, brine and dried (MgSO4). LCMS 368.1 (M+1).

出典