반응 #44005

반응 방정식

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

용매

HOAc

Et2O

반응 조건

후처리

1. 1
   workup.STIRRINGstirred there for 5 hours
2. 2
   기타to destroy the excess diazomethane
3. 3
   추출the solution was extracted with EtOAc
4. 4
   세척The organic phase was washed with sat NaHCO3, water, brine
5. 5
   건조dried (MgSO4)

실험 절차

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).

출처