Sodium Hydroxide → HCID 57445403, compound

HRID 1993372Notes

Reaction equation

HRID 1993372 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[CH:21]=[CH:20][C:19]([N:22]2[C:26](=[O:27])[CH2:25][CH:24]([C:28]([O:30]C)=[O:29])[CH2:23]2)=[CH:18][CH:17]=1.[OH-].[Na+]>CO.C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[CH:17]=[CH:18][C:19]([N:22]2[C:26](=[O:27])[CH2:25][CH:24]([C:28]([OH:30])=[O:29])[CH2:23]2)=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68420806HCID 68420806, compound

Product 1

HCID 57445403HCID 57445403, compound

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of methyl 1-(4-(6,7-dimethoxyquinolin-4-yloxy)phenyl)-5-oxopyrrolidine-3-carboxylate (Step 2, 0.5 ng, 1.18 mmol) in MeOH/THF (2 mL: 2 mL) solution was added 1.77 mL of 1 N NaOH. The reaction was stirred at RT for 8 h. The solution was concentrated in vacuo to dryness and acidified with 1 N HCl. The white precipitate was collected by filtration and washed with 50% EtOAc/hexanes to give the title compound as white solid. MS (ESI pos. ion) m/z: 409.3 (M+H). Calc'd Exact Mass for C22H20N2O6: 408.4.

Workup

  1. concentrationThe solution was concentrated in vacuo to dryness
  2. filtrationThe white precipitate was collected by filtration
  3. washwashed with 50% EtOAc/hexanes

Sources & evidence

ORD record
ord-7dc35d3b40db447697cc3b7fe163c0d7
Source dataset
uspto-grants-2010_01
Patent number
US07652009B2

Reaction notes

Loading…