N-benzyl-4-fluorophenyl-1,4-oxazin-2-one → N-benzyl-3-(S)-(4-fluorophenyl)-1,4-oxazin-2-one

HRID 1378672Notes

Reaction equation

HRID 1378672 reaction equation
[CH2:1]([N:8]1[CH:13]=[CH:12][O:11][C:10](=[O:14])[CH:9]1[C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(OC(C)C)(=O)C>[CH2:1]([N:8]1[CH:13]=[CH:12][O:11][C:10](=[O:14])[C@@H:9]1[C:15]1[CH:16]=[CH:17][C:18]([F:21])=[CH:19][CH:20]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 10924050N-benzyl-4-fluorophenyl-1,4-oxazin-2-one

Product 1

HCID 10924051N-benzyl-3-(S)-(4-fluorophenyl)-1,4-oxazin-2-one

Reagents, catalysts & solvents 1

HCID 7915Isopropyl AcetateSolvent3×

Procedure

A solution of N-benzyl-4-fluorophenyl-1,4-oxazin-2-one (5 g) in isopropyl acetate (16.76 ml) was diluted with isopropyl acetate (37.6 ml) and a solution of (-)-3-bromocamphor-8-sulphonic acid ((-)-3-BCS) (5.73 g) in isopropyl acetate (20.67 ml) added at room temperature. Crystallisation began after approximately 20 minutes. The mixture was stirred for 1 hour at room temperature and then stirred at 75° C. for 9 days. The mixture was then cooled to room temperature, aged at 0°-5° C. for 1 hour and the solid collected, washed with isopropyl acetate to give the N-benzyl-3-(S)-(4-fluorophenyl)-1,4-oxazin-2-one (-)-3-BCS salt: yield 10.5 g, ee 96.5% (S) isomer.

Workup

  1. customCrystallisation
  2. stirringstirred at 75° C. for 9 days
  3. temperatureThe mixture was then cooled to room temperature
  4. waitaged at 0°-5° C. for 1 hour
  5. customthe solid collected
  6. washwashed with isopropyl acetate

Sources & evidence

ORD record
ord-a7dbeac19d574279ad01fd1d20fe7762
Source dataset
uspto-grants-1997_09
Patent number
US05668280

Reaction notes

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