HCID 68959443, compound → HCID 57667996, compound

HRID 2191703Notes

Reaction equation

HRID 2191703 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([NH:10][C:11]3[CH:23]=[C:22]([CH2:24][CH2:25][C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[CH:21]=[CH:20][C:12]=3[C:13]([O:15]C(C)(C)C)=[O:14])=[CH:9][C:4]=2[O:3][CH2:2]1>FC(F)(F)C(O)=O>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([NH:10][C:11]3[CH:23]=[C:22]([CH2:24][CH2:25][C:26]4[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=4)[CH:21]=[CH:20][C:12]=3[C:13]([OH:15])=[O:14])=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

3

Reactant 1

HCID 68959443HCID 68959443, compound

Product 1

HCID 57667996HCID 57667996, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To toluene 3.0 mL solution of tert-butyl 2-amino-4-phenethylbenzoate 0.10 g were added 1-iodo-3,4-methylenedioxybenzene 0.14 g,cesium carbonate 0.22 g, tris(dibenzylideneacetone)dipalladium(0) 3 mg and 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl 8 mg,and it was stirred at 110° C. for 24 hours. After the reaction mixture was cooled to room temperature, tris(dibenzylideneacetone)dipalladium(0) 3 mg and 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl 8 mg were added to it, and it was stirred at 110° C. for 24 hours. After the reaction mixture was cooled to room temperature, ethyl acetate and 10% citric acid aqueous solution were added to it. The organic layer was separated and collected,dried over anhydrous magnesium sulfate after washing with saturated sodium chloride aqueous solution, and the solvent was removed under reduced pressure. The obtained residue was refined by silica gel column chromatography [Trikonex company, Flash Tube 2008, eluent; hexane:ethyl acetate=4:1] to give tert-butyl 2-((benzo-1,3-dioxol-5-yl)amino)-4-phenethylbenzoate. Trifluoroacetic acid 10 mL was added to the obtained tert-butyl 2-((benzo-1,3-dioxol-5-yl)amino)-4-phenethylbenzoate, and it was stirred at room temperature for 2 hours. The solvent was removed under reduced pressure, and the obtained residue was refined by reversed-phase silica gel column chromatography [eluent; 80-100% acetonitrile/0.1% trifluoroacetic acid aqueous solution] to give 2-((benzo-1,3-dioxol-5-yl)amino)-4-phenethylbenzoic acid 12 mg of white solid.

Workup

  1. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-3d52a8b3e3ab4e5682be8ec159abefd3
Source dataset
uspto-grants-2012_12
Patent number
US08327467B2

Reaction notes

Loading…