Water → HCID 15023211, compound

HRID 847336Notes

Reaction equation

HRID 847336 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:22]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:20]=[C:19]([F:27])[C:5]=1[O:6][C:7]1[CH:18]=[CH:17][C:10]2[NH:11][C:12](=[O:16])[C@@H:13]([CH3:15])[O:14][C:9]=2[CH:8]=1.O.[CH3:29]I>CN(C)C=O>[Cl:3][C:4]1[CH:22]=[C:21]([C:23]([F:24])([F:25])[F:26])[CH:20]=[C:19]([F:27])[C:5]=1[O:6][C:7]1[CH:18]=[CH:17][C:10]2[N:11]([CH3:29])[C:12](=[O:16])[C@@H:13]([CH3:15])[O:14][C:9]=2[CH:8]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 15023207HCID 15023207, compound

Product 1

HCID 15023211HCID 15023211, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Then, 60% sodium hydride (0.03 g) was suspended in dimethylformamide (5 ml), and a solution of the abovedescribed 7-(2-chloro-6-fluoro-4-trifluoromethylphenoxy)-2(R)-methyl-2H-1,4-benzoxazine-3 (4H)-one (0.3 g) in dimethylformamide (5 ml) was dropwise added thereto while cooling with water. The mixture was stirred for 10 min, methyl iodide (0.1 g) was added thereto, and the mixture was stirred for an additional 10 min. Water (10 ml) was added thereto to terminate the reaction, and the reaction mixture was extracted with ethyl acetate (20 ml×2), washed with water and a saturated saline solution and dried over anhydrous magnesium sulfate. The solvent was distilled off in vacuo, and the residue was purified by silica gel column chromatography (developing solvent: n-hexane/ethyl acetate=3/1) to prepare the title compound (0.3 g) as a colorless crystal. The compound thus prepared was subjected to HPLC analysis for chiral separation and found to be in agreement with the first eluted fraction in the case of racemate (Example 26) modification and have an optical purity of 80%.

Workup

  1. stirringthe mixture was stirred for an additional 10 min
  2. customto terminate
  3. customthe reaction
  4. extractionthe reaction mixture was extracted with ethyl acetate (20 ml×2)
  5. washwashed with water
  6. dry with materiala saturated saline solution and dried over anhydrous magnesium sulfate
  7. distillationThe solvent was distilled off in vacuo
  8. customthe residue was purified by silica gel column chromatography (developing solvent: n-hexane/ethyl acetate=3/1)
  9. customto prepare the title compound (0.3 g) as a colorless crystal
  10. customThe compound thus prepared
  11. customwas subjected to HPLC analysis for chiral separation

Sources & evidence

ORD record
ord-7594ffd3581b4c23b3375446fd900200
Source dataset
uspto-grants-1992_08
Patent number
US05141551

Reaction notes

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