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Water → 3-[5-(3-{(Benzylamino]carbonylamino}propoxy)indolyl]propanoic acid

HRID 23988
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HRID 23988 반응식
[CH2:1]([NH:8][C:9]([NH:11][CH2:12][CH2:13][CH2:14][O:15][C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[NH:21][C:20]([CH2:25][CH2:26][C:27]([O:29]C)=[O:28])=[CH:19]2)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[OH-].[Na+]>O1CCCC1>[CH2:1]([NH:8][C:9]([NH:11][CH2:12][CH2:13][CH2:14][O:15][C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[NH:21][C:20]([CH2:25][CH2:26][C:27]([OH:29])=[O:28])=[CH:19]2)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 22570288Methyl 3-[5-(3-{[benzylamino]carbonylamino}propoxy)indolyl]propanoate

생성물 1

HCID 225703513-[5-(3-{(Benzylamino]carbonylamino}propoxy)indolyl]propanoic acid수율 82.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To the solution of methyl 3-[5-(3-{[benzylamino]carbonylamino}propoxy)indolyl]propanoate (80 mg, 0.2 mmol), as prepared in the preceding step, in tetrahydrofuran (5 mL) and water (5 mL) was added sodium hydroxide (20 mg), and the reaction mixture was stirred at ambient temperature for 2 h. After evaporating the tetrahydrofuran, the aqueous solution was acidified (pH 5-6), the white solid formed was collected, washed with water and dried under high vacuum to give the title compound (65 mg, 82%). 1H-NMR (400 MHz, DMSO6) δ 7.21 -7.37 (m, 7H), 7.02 (d, J=2.4 Hz, 1H), 6.78 (dd, J=8.8, 2.4 Hz, 1H), 6.36 (t, J=6.0 Hz, 1H), 6.30 (d, J=2.9 Hz, 1H), 6.06 (t, J=5.7 Hz, 1H), 4.34 (t, J=6.8 Hz, 2H), 4.20 (d, J=6.0 Hz, 2H), 3.96 (t, J=6.2 Hz, 2H), 3.19 (q, J=6.4 Hz, 2H), 2.71 (t, J=6.8 Hz, 2H), 1.83 (t, J=6.5 Hz, 2H). Mass spectrum (LCMS, ESI) Calcd. for C22H25N3O4 396.4 (M+H), found: 396.1.

후처리

  1. customAfter evaporating the tetrahydrofuran
  2. customthe white solid formed
  3. customwas collected
  4. washwashed with water
  5. customdried under high vacuum

출처 및 근거

ORD 기록
ord-86a0d22b537640e1bd081d2e5a6a95a6
출처 데이터셋
uspto-grants-2005_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06855722B2

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