Sodium Hydroxide → HCID 60172237, compound

HRID 1403556Notes

Reaction equation

HRID 1403556 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]([N:18]3[CH2:23][CH2:22][O:21][CH2:20][C@@H:19]3[CH3:24])=[N:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:25]([O:27]C)=[O:26])[CH:14]=3)[N:9]=2)=[CH:4][CH:3]=1.[OH-].[Na+]>CO.C(Cl)(Cl)Cl.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]([N:18]3[CH2:23][CH2:22][O:21][CH2:20][C@@H:19]3[CH3:24])=[N:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:25]([OH:27])=[O:26])[CH:14]=3)[N:9]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 60171354HCID 60171354, compound

Product 1

HCID 60172237HCID 60172237, compoundYield 68%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

To a solution of (S)-methyl 2-(4-fluorophenyl)-3-(3-methylmorpholino)quinoxaline-6-carboxylate (140.0 mg, 0.37 mmol,) in methanol (15 mL) and CHCl3 (5 mL) was added a solution of NaOH (45 mg, 1.12 mmol) in water (1 mL). The resulting solution was stirred overnight at room temperature and concentrated in vacuo. The residue was dissolved in water (10 mL) and adjusted to pH 6 with hydrochloric acid (1N). The solids were collected by filtration to afford (S)-2-(4-fluorophenyl)-3-(3-methylmorpholino)quinoxaline-6-carboxylic acid as a yellow solid (91.2 mg, 68%).

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in water (10 mL)
  3. filtrationThe solids were collected by filtration

Sources & evidence

ORD record
ord-4411d8cb3f184684841817f4663705ed
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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