3,5-Difluorophenylacetic acid → (s)-2-[1-(3,5-Difluorophenylacetamido)ethyl]-5(r,s)-ethoxycarbonyl-2-oxazoline

HRID 23016

Reaction equation

HRID 23016 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([OH:12])=O)[CH:5]=[C:6]([F:8])[CH:7]=1.[NH2:13][C@H:14]([C:16]1[O:17][CH:18]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:19][N:20]=1)[CH3:15]>CO.C(Cl)(Cl)Cl>[F:8][C:6]1[CH:5]=[C:4]([CH2:9][C:10]([NH:13][C@H:14]([C:16]2[O:17][CH:18]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:19][N:20]=2)[CH3:15])=[O:12])[CH:3]=[C:2]([F:1])[CH:7]=1

Participants

4

Reactant 2

HCID 1454243,5-Difluorophenylacetic acidHCID 131723742(s)-2-(1-Aminoethyl)-5(r,s)-ethoxycarbonyl-2-oxazoline

Product 1

HCID 131723741(s)-2-[1-(3,5-Difluorophenylacetamido)ethyl]-5(r,s)-ethoxycarbonyl-2-oxazoline

Reagents, catalysts & solvents 1

HCID 21584188Chloroform methanolSolvent

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.

Workup

  1. customthe product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-c299ca4730364ed6b87f71d07b1e409a
Source dataset
uspto-grants-2005_02
Patent number
US06849650B2

Linked notes

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