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

HRID 1178006

反応式

HRID 1178006 の反応式
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]

参加物

8

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

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%

後処理

  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

出典と根拠

ORDレコード
ord-315ffd713d4f4706878d916779215f0a
出典データセット
uspto-grants-2010_11
特許番号
US07842696B2

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