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

HRID 1378671Notes

Reaction equation

HRID 1378671 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.C(#N)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

4

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 2

HCID 6342AcetonitrileSolventHCID 7915Isopropyl AcetateSolvent

Procedure

To a solution of N-benzyl-4-fluorophenyl-1,4-oxazin-2-one (10 g) in isopropyl acetate (110 ml) at room temperature was added a solution of (-)-3-bromocamphor-8-sulphonic acid ((-)-3-BCS) (12 g) in acetonitrile (24 ml). Crystallisation began after 2-3 minutes. The slurry was stirred for 1 hour at room temperature. Trifluoroacetic acid (7 ml) was added and the mixture stirred at 65° C. for 3 days. The mixture was cooled to 0°-5° C., aged for 1 hour and the solid collected, washed with isopropyl acetate and dried in vacuo at 40° C., to give the N-benzyl-3-(S)-(4-fluorophenyl)-1,4-oxazin-2-one (-)-3-BCS salt: yield 17.24 g, ee 98.6% (S) isomer.

Workup

  1. customCrystallisation
  2. additionTrifluoroacetic acid (7 ml) was added
  3. stirringthe mixture stirred at 65° C. for 3 days
  4. temperatureThe mixture was cooled to 0°-5° C.
  5. waitaged for 1 hour
  6. customthe solid collected
  7. washwashed with isopropyl acetate
  8. customdried in vacuo at 40° C.

Sources & evidence

ORD record
ord-76da1f56d4ee4c3b81935db0ed77a2da
Source dataset
uspto-grants-1997_09
Patent number
US05668280

Reaction notes

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