Reaction #11044

ord-eeba8983ef704b9db8cf16948c3268c1

Reaction equation

COC(=O)[C@H](Cc1ccc(-c2cccc(N)c2)cc1)NS(=O)(=O)c1c(C)cc(C)cc1C
Methyl (2S)-3-(3′-amino[1,1′-biphenyl]-4-yl)-2-mesitylsulfonylamino-propanoate
CCOc1c(OCC)c(=O)c1=O
3,4-diethoxy-3-cyclobuten-1,2-dion
→
CCOc1c(Nc2cccc(-c3ccc(C[C@H](NS(=O)(=O)c4c(C)cc(C)cc4C)C(=O)OC)cc3)c2)c(=O)c1=O
title compound
Yield 59.0%
CCOc1c(Nc2cccc(-c3ccc(C[C@H](NS(=O)(=O)c4c(C)cc(C)cc4C)C(=O)OC)cc3)c2)c(=O)c1=O
Methyl (2S)-3-{3′-[(2-ethoxy-3,4-dioxo-1-cyclobuten-1-yl)-amino][1,1′-biphenyl]-4-yl}-2-mesitylsulfonylamino-propanoate
Yield 59.0%

Reactants

COC(=O)[C@H](Cc1ccc(-c2cccc(N)c2)cc1)NS(=O)(=O)c1c(C)cc(C)cc1C
Methyl (2S)-3-(3′-amino[1,1′-biphenyl]-4-yl)-2-mesitylsulfonylamino-propanoate
CCOc1c(OCC)c(=O)c1=O
3,4-diethoxy-3-cyclobuten-1,2-dion

Reagents

None

Solvents

CCCO
1 propanol

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Temperaturerefluxed for 20 h
  2. 2
    OtherPurification by flash chromatography (dichloromethane/acetic acid ethyl ester 10+1)

Procedure

2 g of Methyl (2S)-3-(3′-amino[1,1′-biphenyl]-4-yl)-2-mesitylsulfonylamino-propanoate 12.1.2 were mixed with 0.75 g 3,4-diethoxy-3-cyclobuten-1,2-dion in 40 ml 1 propanol and refluxed for 20 h. Purification by flash chromatography (dichloromethane/acetic acid ethyl ester 10+1) yielded 1,5 g of the title compound.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07094911B2uspto-grants-2006_08