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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
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HRID 2091215 반응식
[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
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참가 물질

8

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8471Triethylamine용매

실험 절차

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

후처리

  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)

출처 및 근거

ORD 기록
ord-003c0fc8e5d243f0beb3730a24ecffbf
출처 데이터셋
uspto-grants-2013_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08436043B2

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