Reaktion #499656

Reaktionsgleichung

bromo-tris(pyrrolidino)phosphonium hexafluorophosphate

(R)-3-{4-[(4-tert-butylcyclohexylamino)methyl]benzoylamino}-2-hydroxypropionic acid

4-(trifluoromethoxy)phenylacetic acid

diisopropylethylamine

→

title compound

(R)-3-[4-({(4-tert-butylcyclohexyl)-[2-(4-trifluoromethoxyphenyl)acetyl]-amino}methyl)benzoylamino]-2-hydroxypropionic Acid

Lösungsmittel

1,2-dichloropropane

1,2-dichloropropane

N-methyl-2-pyrrolidinone

1,2-dichloropropane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Filtrationfollowed by filtration
2. 2
   workup.ADDITIONwas added
3. 3
   Sonstigeto react for 3 hours at 50° C.
4. 4
   Waschenwhile washed with N-methyl-2-pyrrolidinone (4×1 mL), and DCM (10×1 mL)
5. 5
   Sonstigeafforded the resin

Vorschrift

The above resin bound (R)-3-{4-[(4-tert-butylcyclohexylamino)methyl]benzoylamino}-2-hydroxypropionic acid was added 1,2-dichloropropane (500 μL) and BSA (100 μL) and the mixture was vortexed at 25° C. for 1 hour followed by filtration. To the resin was added a solution of 4-(trifluoromethoxy)phenylacetic acid (400 umol) in a mixture of N-methyl-2-pyrrolidinone, 1,2-dichloropropane and diisopropylethylamine (4.5:4.5:1, 1 mL) was added followed by a solution of bromo-tris(pyrrolidino)phosphonium hexafluorophosphate (400 μmol) in 1,2-dichloropropane (500 μL). The mixture was allowed to react for 3 hours at 50° C. and the resin was allowed to cool to 25° C. while washed with N-methyl-2-pyrrolidinone (4×1 mL), and DCM (10×1 mL) afforded the resin bound title compound.

Quelle