Lithium Hydroxide → HCID 42602179, compound

HRID 2067163Notes

Reaction equation

HRID 2067163 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH3:17])[CH:11]=2)=[CH:4][C:3]=1[C:18]([NH:20][CH2:21][C:22]1[CH:31]=[CH:30][C:25]([C:26]([O:28]C)=[O:27])=[CH:24][CH:23]=1)=[O:19].[OH-].[Li+]>O1CCOCC1.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH3:17])[CH:11]=2)=[CH:4][C:3]=1[C:18]([NH:20][CH2:21][C:22]1[CH:23]=[CH:24][C:25]([C:26]([OH:28])=[O:27])=[CH:30][CH:31]=1)=[O:19]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 59608440HCID 59608440, compound

Product 1

HCID 42602179HCID 42602179, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of methyl 4-[({[2-chloro-5-({[3-(methyloxy)phenyl]methyl}oxy)phenyl]carbonyl}amino)methyl]benzoate (106 mg, 0.24 mmol) and lithium hydroxide (2 eq, 20 mg, 0.48 mmol) in dioxane (3 ml) and H2O (1.5 ml) was heated at 65° C. for 3 hours. On cooling solvent was evaporated in vacuo, residue acidified with 2M HCl and filtered to give the title compound as a white solid. MS (ES+) m/z 426 [M+H]+ (C23H2035ClNO5). 1H-NMR (400 MHz, d6-DMSO) δ 3.76 (3H, s), 4.50 (2H, d, J 6), 5.12 (2H, s), 6.91 1H, dd, J 1.6, J 7.6), 7.02 (1H, s), 7.09 (2H, m), 7.30 (1H, t, J 4), 7.40-7.47 (2H, m), 7.92 (2H, d, J 8), 9.04 (1H, t, J 6)

Workup

  1. temperatureOn cooling solvent
  2. customwas evaporated in vacuo, residue
  3. filtrationfiltered

Sources & evidence

ORD record
ord-2a9bff2711914e87ba355cd276a79cef
Source dataset
uspto-grants-2012_10
Patent number
US08293798B2

Reaction notes

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