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

HRID 23988Notes

Reaction equation

HRID 23988 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-86a0d22b537640e1bd081d2e5a6a95a6
Source dataset
uspto-grants-2005_02
Patent number
US06855722B2

Reaction notes

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