Reaktion #44005

Reaktionsgleichung

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

Lösungsmittel

HOAc

Et2O

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGstirred there for 5 hours
2. 2
   Sonstigeto destroy the excess diazomethane
3. 3
   Extraktionthe solution was extracted with EtOAc
4. 4
   WaschenThe organic phase was washed with sat NaHCO3, water, brine
5. 5
   Trocknendried (MgSO4)

Vorschrift

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).

Quelle