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Water → Ethyl 3-{[(4-{[(5-methoxy-3-methyl-1-benzofuran-2-yl)(phenyl)methyl]amino}phenyl)carbonyl](methyl)amino}-propanoate

HRID 2091215
ノート
印刷プレビュー

反応式

HRID 2091215 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9]([CH:11]([NH:18][C:19]3[CH:27]=[CH:26][C:22](C(O)=O)=[CH:21][CH:20]=3)[C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[C:8]([CH3:28])[C:7]=2[CH:29]=1.CNC[CH2:33][C:34]([O:36]CC)=O.[OH2:39].ON1C2C=CC=CC=2N=N1.Cl.C(N=C=N[CH2:56][CH2:57][CH2:58][N:59]([CH3:61])[CH3:60])C.[OH2:62]>CN(C)C=O.C(N(CC)CC)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9]([CH:11]([NH:18][C:19]3[CH:20]=[CH:21][C:22]([C:61]([N:59]([CH3:60])[CH2:58][CH2:57][C:56]([O:36][CH2:34][CH3:33])=[O:62])=[O:39])=[CH:26][CH:27]=3)[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)=[C:8]([CH3:28])[C:7]=2[CH:29]=1
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 962WaterHCID 541480Ethyl 3-(methylamino)propanoateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 667776604-{[(5-Methoxy-3-methyl-1-benzofuran-2-yl)(phenyl)methyl]amino}benzoic acid

生成物 1

HCID 66777122
Ethyl 3-{[(4-{[(5-methoxy-3-methyl-1-benzofuran-2-yl)(phenyl)methyl]amino}phenyl)carbonyl](methyl)amino}-propanoate
収率 94%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8471Triethylamine溶媒

実験手順

To a mixture of 4-{[(5-methoxy-3-methyl-1-benzofuran-2-yl)(phenyl)methyl]amino}benzoic acid (400 mg) synthesized above, ethyl 3-(methylamino)propanoate (203 mg), 1-hydroxybenzotriazole monohydrate (237 mg), triethylamine (431 μL) and N,N-dimethylformamide (10 mL) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (297 mg), and the mixture was stirred overnight at room temperature. Water was added to quench the reaction, and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (30-70% ethyl acetate/hexane) to give the title object compound (486 mg, 94%) as a pale-brown oil

後処理

  1. customto quench
  2. customthe reaction
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (30-70% ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-003c0fc8e5d243f0beb3730a24ecffbf
出典データセット
uspto-grants-2013_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08436043B2

反応ノート

読み込み中…

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