Diethyl squarate → Methyl (2S)-3-{3'-[(2-ethoxy-3,4-dioxo-1-cyclobuten-1-yl) amino][1,1'-biphenyl]-4-yl}-2-mesitylsulfonylamino-propanoate

HRID 10948Notes

Reaction equation

HRID 10948 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][C@H:15]([NH:20][S:21]([C:24]3[C:29]([CH3:30])=[CH:28][C:27]([CH3:31])=[CH:26][C:25]=3[CH3:32])(=[O:23])=[O:22])[C:16]([O:18][CH3:19])=[O:17])=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.[CH2:33]([O:35][C:36]1[C:37](=O)[C:38](=[O:43])[C:39]=1[O:40]CC)[CH3:34]>C(O)CC>[CH2:33]([O:35][C:36]1[C:39](=[O:40])[C:38](=[O:43])[C:37]=1[NH:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][C@H:15]([NH:20][S:21]([C:24]3[C:29]([CH3:30])=[CH:28][C:27]([CH3:31])=[CH:26][C:25]=3[CH3:32])(=[O:23])=[O:22])[C:16]([O:18][CH3:19])=[O:17])=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1)[CH3:34]

Participants

4

Reactant 2

HCID 123228Diethyl squarateHCID 11430900HCID 11430900, compound

Product 1

HCID 56989219Methyl (2S)-3-{3'-[(2-ethoxy-3,4-dioxo-1-cyclobuten-1-yl) amino][1,1'-biphenyl]-4-yl}-2-mesitylsulfonylamino-propanoateYield 59%

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

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.

Workup

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

Sources & evidence

ORD record
ord-eeba8983ef704b9db8cf16948c3268c1
Source dataset
uspto-grants-2006_08
Patent number
US07094911B2

Reaction notes

Loading…