Tetrahydrofuran → HCID 21830395, compound

HRID 1601065Notes

Reaction equation

HRID 1601065 reaction equation
[N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][C:2]=1[CH2:10][NH:11][C:12]([C:14]1[CH:31]=[CH:30][C:17]2[CH2:18][CH:19]([CH2:25][C:26]([O:28]C)=[O:27])[C:20](=[O:24])[N:21]([CH3:23])[CH2:22][C:16]=2[CH:15]=1)=[O:13].O[Li].O.C1COCC1>O>[N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][C:2]=1[CH2:10][NH:11][C:12]([C:14]1[CH:31]=[CH:30][C:17]2[CH2:18][CH:19]([CH2:25][C:26]([OH:28])=[O:27])[C:20](=[O:24])[N:21]([CH3:23])[CH2:22][C:16]=2[CH:15]=1)=[O:13]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 53681569HCID 53681569, compound

Product 1

HCID 21830395HCID 21830395, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of methyl (±)-8-[[[(2-benzimidazolyl)methyl]amino]carbonyl]-2-methyl-3-oxo-2,3,4,5-tetrahydro-1H-2-benzazepine-4-acetate (0.10 g, 0.24 mmol), LiOH.H2O (0.013 g, 0.31 mmol), THF (2 mL), and H2O (2 mL) was stirred at RT for 18 h, then was concentrated to dryness. The residue was dissolved in H2O, and the solution was brought to pH 4-5 with 3N HCl. The resulting precipitate was collected by filtration and dried. Recrystallization from boiling isopropanol gave the title compound (0.035 g, 36%) as a colorless solid: 1H NMR (DMSO-d6) δ 9.13 (t, J=5.7 Hz, 1H), 7.79 (m, 1H), 7.48 (m, 2H), 7.23 (d, J=7.9 Hz, 1H), 7.14 (m, 2H), 5.32 (d, J=16.9 Hz, 1H), 4.69 (d, J=5.7 Hz, 2H), 4.03 (d, J=16.7 Hz, 1H), 3.79 (m, 1H), 3.14 (dd, J=18, 2 Hz, 1H), 2.90 (s, 3H), 2.70 (m, 2H), 2.38 (dd, J=11.4, 3 Hz, 1H); MS (ES) m/e 407 (M+H)+. Anal. Calcd for C22H22N4O4.1.5 H2O.0.5 C3H8O: C, 60.90; H, 6.31; N, 12.09. Found: C, 60.68; H, 6.05; N, 12.05.

Workup

  1. concentrationwas concentrated to dryness
  2. dissolutionThe residue was dissolved in H2O
  3. filtrationThe resulting precipitate was collected by filtration
  4. customdried
  5. customRecrystallization

Sources & evidence

ORD record
ord-ac3ee5bed98745be9e00feee34a80d19
Source dataset
uspto-grants-1999_11
Patent number
US05977101

Reaction notes

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