Lithium Hydroxide → HCID 21830385, compound

HRID 1601077Notes

Reaction equation

HRID 1601077 reaction equation
[Li+].[OH-].[NH:3]1[CH:7]=[CH:6][N:5]=[C:4]1[CH2:8][NH:9][C:10]([C:12]1[CH:13]=[CH:14][C:15]2[NH:21][CH:20]([CH2:22][C:23]([O:25]C)=[O:24])[C:19](=[O:27])[N:18]([CH2:28][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH2:17][C:16]=2[CH:36]=1)=[O:11]>O1CCOCC1.O>[NH:3]1[CH:7]=[CH:6][N:5]=[C:4]1[CH2:8][NH:9][C:10]([C:12]1[CH:13]=[CH:14][C:15]2[NH:21][CH:20]([CH2:22][C:23]([OH:25])=[O:24])[C:19](=[O:27])[N:18]([CH2:28][CH2:29][C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)[CH2:17][C:16]=2[CH:36]=1)=[O:11]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 54316335HCID 54316335, compound

Product 1

HCID 21830385HCID 21830385, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
65 °C

Procedure

LiOH (16 mg, 0.38 mmol) was added at RT to a solution of methyl (±)-7-[[[(2-imidazolyl)methyl]amino]carbonyl]-3-oxo-4-(2-phenylethyl)-2,3,4,5-tetrahydro-1H-1,4-benzodiazepine-2-acetate (98 mg, 0.21 mmol) in dioxane (3 mL) and H2O (3 mL). The reaction mixture was heated at 65° C. for 3 h then the organic solvent was removed in vacuo. The aqueous residue was acidified with 1M HCl solution (0.38 mL) to obtain a white solid which was filtered, dissolved in hot methanol, and precipitated with ether. The thus obtained white solid was collected to yield the title compound (72 mg, 78%). 1H NMR (DMSO-d6, 400 MHz) δ 2.59 (dd, J=16.2, 5.0 Hz, 1H), 2.77 (dd, J=7.7, 6.8 Hz, 2H), 2.92 (dd, J=16.5, 8.8 Hz, 1H), 3.63-3.75 (m, 2H), 3.79 (d, J=16.5 Hz, 1H), 4.61 (s, 2H), 5.13 (dd, J=8.8, 5.0 Hz, 1H), 5.45 (d, J=16.5 Hz, 1H), 6.57 (d, J=8.6 Hz, 1H), 7.07 (s, 2H), 7.10-7.19 (m, 5H), 7.41 (s, 1H), 7.54 (d, J=8.4 Hz, 1H). MS (ES) m/e 448 (M+H)+. Anal. Calcd. for C24H25N5O4.H2O: C, 61.92; H, 5.85; N, 15.04. Found: C, 61.69; H, 5.60; N, 14.86.

Workup

  1. customthe organic solvent was removed in vacuo
  2. customto obtain a white solid which
  3. filtrationwas filtered
  4. dissolutiondissolved in hot methanol
  5. customprecipitated with ether
  6. customThe thus obtained white solid was collected

Sources & evidence

ORD record
ord-dd0d0db4361e4a91849facff4fd2e78b
Source dataset
uspto-grants-1999_11
Patent number
US05977101

Reaction notes

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