Reaction #51294

ord-c299ca4730364ed6b87f71d07b1e409a

Reaction equation

O=C(O)Cc1cc(F)cc(F)c1
3,5-difluorophenylacetic acid
CCOC(=O)C1CN=C([C@H](C)N)O1
(S)-2-(1-aminoethyl)-5(R,S)-ethoxycarbonyl-2-oxazoline
→
CCOC(=O)C1CN=C([C@H](C)NC(=O)Cc2cc(F)cc(F)c2)O1
title compound
CCOC(=O)C1CN=C([C@H](C)NC(=O)Cc2cc(F)cc(F)c2)O1
(S)-2-[1-(3,5-difluorophenylacetamido)ethyl]-5(R,S)-ethoxycarbonyl-2-oxazoline

Reactants

O=C(O)Cc1cc(F)cc(F)c1
3,5-difluorophenylacetic acid
CCOC(=O)C1CN=C([C@H](C)N)O1
(S)-2-(1-aminoethyl)-5(R,S)-ethoxycarbonyl-2-oxazoline

Reagents

None

Solvents

CO.ClC(Cl)Cl
MeOH CHCl3

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Otherthe product was purified by silica gel chromatography

Procedure

Following General Procedure A and using 3,5-difluorophenylacetic acid (Aldrich) and (S)-2-(1-aminoethyl)-5(R,S)-ethoxycarbonyl-2-oxazoline (Example F), the title compound was prepared as a semisolid. The reaction was monitored by tlc (Rf=0.3 in 5% MeOH/CHCl3) and the product was purified by silica gel chromatography using 5% MeOH/CHCl3 as the eluent.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06849650B2uspto-grants-2005_02