Dimethyl Sulfoxide → 1,1,1-Trifluoro-3-[(N-acetylprolyl)alanylprolylamino]-butane-2,2-diol

To a solution of oxalyl chloride (72 μl, 0.83 mmol) in methylene chloride (1 ml) under an argon atmosphere and cooled in a dry ice-acetone bath was added dimethylsulfoxide (0.12 ml, 1.65 mmol) with stirring. After 5 minutes, a solution of the compound of example 57 (0.25 g, 0.55 mmol) in methylene chloride (1.5 ml) was added. The reaction mixture was stirred for 15 minutes, triethylamine (0.50 ml,3.58 mmol) then added and the reaction warmed to room temperature for 30 minutes. The reaction mixture was placed directly onto a silica gel column and eluted with methylene chloride-methanol. Trituration of the resultant oily solid with ether-hexane and filtration gave the above-named product, (50 mg, 0.11 mmol).

1. stirringThe reaction mixture was stirred for 15 minutes
2. washeluted with methylene chloride-methanol
3. filtrationTrituration of the resultant oily solid with ether-hexane and filtration
4. customgave the above-named product, (50 mg, 0.11 mmol)

ORD-Eintrag

ord-7b21a6534ee34fdc9aa278ce119014f1

Quelldatensatz

uspto-grants-1998_12

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US05849866