Reaction #657347

Reaction equation

CHCl3

Methyl N-{[(9H-fluoren-9-ylmethyl)oxy]carbonyl}-L-α-aspartyl chloride

[2-amino-5-(methyloxy)phenyl](4-chlorophenyl)methanone

→

Methyl N1-[2-[(4-chlorophenyl)carbonyl]-4-(methyloxy)phenyl]-N2-{[(9H-fluoren-9-ylmethyl)oxy]carbonyl}-L-α-asparaginate

Conditions

Workup

1. 1
   Temperaturebefore being cooled
2. 2
   Concentrationconcentrated under reduced pressure
3. 3
   Otherused without further purification

Procedure

A mixture of Methyl N-{[(9H-fluoren-9-ylmethyl)oxy]carbonyl}-L-α-aspartyl chloride (prepared from J. Org. Chem. 1990, 55, 3068-3074 and J. Chem. Soc. Perkin Trans. 1 2001, 1673-1695) (221 g, 0.57 mol) and [2-amino-5-(methyloxy)phenyl](4-chlorophenyl)methanone (for a preparation see Intermediate 7) (133 g, 0.5 mol) in CHCl3 (410 mL) was stirred at 60° C. for 1.5 h before being cooled and concentrated under reduced pressure and used without further purification. LC/MS: m/z 613 [M(35Cl)+H]+, Rt=3.89 min.

Source