Dimethyl Sulfoxide → 3-[(N-acetylprolyl)alanylprolylamino]-2,2-dihydroxybutanoic acid, methyl ester

To a stirred solution of oxalyl chloride (0.12 ml, 1.43 mmol) in methylene chloride (1.5 ml) under an argon atmosphere and cooled in a dry ice-acetone bath was added dropwise a solution of dimethylsulfoxide (0.20 ml, 2.86 mmol) in methylene chloride (1.5 ml). After 5 minutes, a solution of the product of example 59 (0.32 g, 0.72 mmol) in methylene chloride (1.5 ml) was added and the reaction mixture stirred for 25 minutes. Triethylamine (0.50 ml, 3.58 mmol) was added and the reaction mixture warmed to room temperature. The reaction mixture was placed directly onto a silica gel column and eluted with methylene chloride-methanol. Evaporation of the appropriate fractions on a rotary evaporator, addition of water (3 ml) to the residue and evaporation gave the above-namedproduct.

1. washeluted with methylene chloride-methanol
2. customEvaporation of the appropriate fractions
3. customon a rotary evaporator, addition of water (3 ml)
4. customto the residue and evaporation
5. customgave the above-namedproduct

ORD-Eintrag

ord-d50fac0400504deeb61de01fdaf30807

Quelldatensatz

uspto-grants-1996_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US05496927