Hydrochloric Acid → N-{[3-(Benzyloxy)phenyl]methyl}-2-([1,1'-biphenyl]-4-yl)acetamide

HRID 1674728Notes

Reaction equation

HRID 1674728 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.C(N(C(C)C)CC)(C)C.F[P-](F)(F)(F)(F)F.N1C2C=CC=C(O[P+](N3CCCC3)(N3CCCC3)N3CCCC3)C=2N=N1.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.Cl.[CH2:93]([O:100][C:101]1[CH:102]=[C:103]([CH:106]=[CH:107][CH:108]=1)[CH2:104][NH2:105])[C:94]1[CH:99]=[CH:98][CH:97]=[CH:96][CH:95]=1.Cl>CN(C)C=O.O>[CH2:93]([O:100][C:101]1[CH:102]=[C:103]([CH:106]=[CH:107][CH:108]=1)[CH2:104][NH:105][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]=1)[C:94]1[CH:95]=[CH:96][CH:97]=[CH:98][CH:99]=1

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 3332FelbinacHCID 81531Diisopropylethylamine2×HCID 2724699PyBOPHCID 19744718[3-(Benzyloxy)phenyl]methanamine hydrochlorideHCID 178506432HCID 178506432, compound

Product 1

HCID 59000621N-{[3-(Benzyloxy)phenyl]methyl}-2-([1,1'-biphenyl]-4-yl)acetamideYield 62.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 4-biphenyl acetic acid (2.29 g, 10.45 mmol) in dimethylformamide, DMF, (30 ml) was added diisopropylethylamine, DIEA, (5.47 ml, 31.35 mmol) and stirred at room temperature for 15 min, then benzotriazolyloxy-tris[pyrrolidino]-phosphonium hexafluorophosphate, PyBOP™, (5.43 g, 10.45 mmol) was added and the stirring was continued for further 30 min, then 3-benzyloxybenzylaminehydrochloride (2.6 g, 10.45 mmol) was added and the stirring continued for 24 hrs. The reaction mixture was then 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 yellowish-white powder of the desired compound (2.65 g) 62% yield.

Workup

  1. waitthe stirring was continued for further 30 min
  2. waitthe stirring continued for 24 hrs
  3. additionThe reaction mixture was then poured on to ice
  4. extractionextracted with ethyl acetate (100 ml)
  5. washthe organic layer washed with saturated solution of NaHCO3, water and brine
  6. dry with materialdried over Na2SO4
  7. customthe solvent removed under vacuum

Sources & evidence

ORD record
ord-8068df183a2641c2beb3f5f241f7556c
Source dataset
uspto-grants-2011_08
Patent number
US08003641B2

Reaction notes

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