Trifluoroacetic anhydride → HCID 58964774, compound

HRID 2120357Notes

Reaction equation

HRID 2120357 reaction equation
[CH3:1][S:2]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:19])[C@:12]([OH:18])([CH3:17])[C:13]([F:16])([F:15])[F:14])=[C:6]([Cl:20])[C:5]=1[F:21])=O.F[C:23](F)(F)C(OC(=O)C(F)(F)F)=O>>[CH2:1]([S:2][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:19])[C@:12]([OH:18])([CH3:17])[C:13]([F:16])([F:15])[F:14])=[C:6]([Cl:20])[C:5]=1[F:21])[CH3:23]

Participants

3

Reactant 2

HCID 9845Trifluoroacetic anhydrideHCID 69824078HCID 69824078, compound

Product 1

HCID 58964774HCID 58964774, compound

Procedure

A suspension of (R)-N-[4-methylsulphinyl-3-fluoro-2-chlorophenyl]-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide (Example 2) (5.41 g) in trifluoroacetic anhydride (65 ml) was heated under reflux for 30 minutes. The reaction mixture was evaporated and the residue was redissolved in MeOH (32 ml) and triethylamine (32 ml) and ethyl iodide (2.2 ml) was added. The reaction mixture was heated under reflux for 3 hours, allowed to cool to room temperature and volatile material was removed by evaporation. The residue was partitioned between EtOAc (150 ml) and brine (100 ml); the organic phase was separated, dried and volatile material was removed by evaporation. The residue was purified by flash column chromatography eluting with 10-20% EtOAc/isohexane to give the title compound (2.16 g) as a yellow solid. NMR (CDCl3) 1.27 (s, 3H), 1.76 (s, 3H), 2.88-2.95 (q, 2H), 3.55 (s, 1H), 7.32 (t, 1H), 8.15 (d, 1H), 8.92 (s, 1H); m/z: 344.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 30 minutes
  3. customThe reaction mixture was evaporated
  4. dissolutionthe residue was redissolved in MeOH (32 ml)
  5. additiontriethylamine (32 ml) and ethyl iodide (2.2 ml) was added
  6. temperatureThe reaction mixture was heated
  7. temperatureunder reflux for 3 hours
  8. customvolatile material was removed by evaporation
  9. customThe residue was partitioned between EtOAc (150 ml) and brine (100 ml)
  10. customthe organic phase was separated
  11. customdried
  12. customvolatile material was removed by evaporation
  13. customThe residue was purified by flash column chromatography
  14. washeluting with 10-20% EtOAc/isohexane

Sources & evidence

ORD record
ord-cdeaff7591f746eda89b3c91ec256e8b
Source dataset
uspto-grants-2004_02
Patent number
US06689909B1

Reaction notes

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