(1,1'-Biphenyl)-4-carboxylic acid → Ethyl 2-[(4-phenylphenyl)carbonylamino]acetate

HRID 1178006

Reaction equation

HRID 1178006 reaction equation
CCN(C(C)C)C(C)C.[C:10]1([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:15]=[CH:14][C:13]([C:16]([OH:18])=O)=[CH:12][CH:11]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.Cl.[CH2:48]([O:50][C:51](=[O:54])[CH2:52][NH2:53])[CH3:49]>CN(C=O)C.O>[CH2:48]([O:50][C:51](=[O:54])[CH2:52][NH:53][C:16]([C:13]1[CH:12]=[CH:11][C:10]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:15][CH:14]=1)=[O:18])[CH3:49]

Participants

8

Reactant 5

HCID 66724(1,1'-Biphenyl)-4-carboxylic acidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2723640Glycine ethyl ester, hydrochlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 2163299Ethyl 2-[(4-phenylphenyl)carbonylamino]acetateYield 87.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

DIPEA (7.825 g, 60.54 mmol) was added to a stirred solution of biphenyl-4-carboxylic acid (4 g, 20.18 mmol) in DMF (40 mL). HOBT (3.27 g, 24.22 mmol) and EDCI.HCl (3.87 mg, 24.22 mmol) were then added at room temperature. After 2 minutes, glycine ethyl ester hydrochloride (3.381 g, 24.22 mmol) was added and the resulting mixture was stirred overnight. The reaction mixture was diluted with cold water and the product was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine solution, dried over sodium sulphate and concentrated under reduced pressure to afford 5 g (87.4% yield) of [(biphenyl-4-carbonyl)-amino]-acetic acid ethyl ester. LC-MS purity: 93.4%

Workup

  1. extractionthe product was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated brine solution
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-315ffd713d4f4706878d916779215f0a
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Linked notes

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