Hydrochloric Acid → [1,1'-Biphenyl]-4-acetamide, N-[(3-fluorophenyl)methyl]-
Reaction equation
[C:1]1([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:6]=[CH:5][C:4]([CH2:7][C:8]([OH:10])=O)=[CH:3][CH:2]=1.CCN(C(C)C)C(C)C.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.[F:59][C:60]1[CH:61]=[C:62]([CH:65]=[CH:66][CH:67]=1)[CH2:63][NH2:64].Cl>CN(C=O)C.O>[F:59][C:60]1[CH:61]=[C:62]([CH:65]=[CH:66][CH:67]=1)[CH2:63][NH:64][C:8](=[O:10])[CH2:7][C:4]1[CH:3]=[CH:2][C:1]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:6][CH:5]=1Participants
8
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of 4-biphenyl acetic acid (2.00 g, 9.42 mmol) in DMF (20 ml) was added DIEA (3.29 ml, 18.84 mmol) and stirred at room temperature for 15 min, then PyBOP (4.90 g, 9.42 mmol) added and the stirring continued for further 30 min, then 3-fluorobenzylamine (1.18 g, 9.42 mmol) added and the stirring continued for 24 hrs, then the reaction mixture poured on to ice cooled water acidified with (10 ml) 1 N HCl and extracted with ethyl acetate (100 ml) and the organic layer washed with saturated solution of NaHCO3, water and brine, dried over Na2SO4 and the solvent removed under vacuum to give a white powder of the desired compound (1.00 g) 33% yield. Another method involves the acid chloride coupling method described below.
Workup
- waitthe stirring continued for further 30 min
- waitthe stirring continued for 24 hrs
- additionthe reaction mixture poured on to ice
- extractionextracted with ethyl acetate (100 ml)
- washthe organic layer washed with saturated solution of NaHCO3, water and brine
- dry with materialdried over Na2SO4
- customthe solvent removed under vacuum
Sources & evidence
- ORD record
- ord-df169b86bc90495d9d342fba1479d423
- Source dataset
- uspto-grants-2012_08
- Patent number
- US08236799B2
Reaction notes
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