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1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → [(Biphenyl-4-carbonyl)-methyl-amino]-acetic acid methyl ester

HRID 1177993
ノート
印刷プレビュー

反応式

HRID 1177993 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.[CH3:47][O:48][C:49](=[O:53])[CH2:50][NH:51][CH3:52]>CN(C=O)C.O>[CH3:47][O:48][C:49](=[O:53])[CH2:50][N:51]([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])[CH3:52]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 66724(1,1'-Biphenyl)-4-carboxylic acidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 83544Glycine, N-methyl-, methyl ester, hydrochloride (1:1)

生成物 1

HCID 43407419[(Biphenyl-4-carbonyl)-methyl-amino]-acetic acid methyl ester
収率 77.7%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

DIPEA (880 mg, 1.2 mL, 6.8 mmol) was added to a stirred solution of biphenyl-4-carboxylic acid (300 mg, 1.5 mmol) in DMF (5 mL). HOBT (224 mg, 1.66 mmol) and EDCI (725 mg, 3.7 mmol) were then added at room temperature. After 2 minutes methylamino-acetic acid methyl ester hydrochloride salt (253 mg, 1.8 mmol) was added and the resulting mixture was stirred at room temperature overnight. Cold water was then added and the product was extracted with EtOAc and the organic layer was washed with brine. The organic phase was dried over Na2SO4 and concentrated under reduced pressure to get the residue. The obtained residue was purified by column chromatography (using silica gel of 60-120 mesh and 20% EtOAc in hexane as eluent) filtered the solid precipitated out to afford 330 mg (76.96% yield) of [(biphenyl-4-carbonyl)-methyl-amino]-acetic acid methyl ester.

後処理

  1. extractionthe product was extracted with EtOAc
  2. washthe organic layer was washed with brine
  3. dry with materialThe organic phase was dried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customto get the residue
  6. customThe obtained residue was purified by column chromatography (using silica gel of 60-120 mesh and 20% EtOAc in hexane as eluent)
  7. filtrationfiltered the solid
  8. customprecipitated out

出典と根拠

ORDレコード
ord-938ce37734e54162b6f9dbe9ec40ac78
出典データセット
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07842696B2

反応ノート

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