m-Chloroperbenzoic acid → HCID 69883400, compound

HRID 2120348Notes

Reaction equation

HRID 2120348 reaction equation
[Cl:1][C:2]1[C:7]([S:8][CH3:9])=[C:6]([S:10]([CH2:13][CH3:14])(=[O:12])=[O:11])[CH:5]=[CH:4][C:3]=1[NH:15][C:16](=[O:24])[C@:17]([OH:23])([CH3:22])[C:18]([F:21])([F:20])[F:19].ClC1C=C(C=CC=1)C(OO)=[O:30].C(=O)([O-])O.[Na+]>C(Cl)Cl>[CH2:13]([S:10]([C:6]1[CH:5]=[CH:4][C:3]([NH:15][C:16](=[O:24])[C@:17]([OH:23])([CH3:22])[C:18]([F:19])([F:21])[F:20])=[C:2]([Cl:1])[C:7]=1[S:8]([CH3:9])=[O:30])(=[O:12])=[O:11])[CH3:14]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acid3×HCID 516892Sodium BicarbonateHCID 9887574HCID 9887574, compound

Product 1

HCID 69883400HCID 69883400, compoundYield 132.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (R)-N-[4-ethylsulphonyl-3-methylsulphanyl-2-chlorophenyl]-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide (Example 28) (0.636 g) in DCM was added metachloroperoxybenzoic acid (0.17 g). After 1 hour at ambient temperature a further portion of meta-chloroperoxybenzoic acid (0.14 g) was added and stirring was continued at ambient temperature for 16 hours. Further meta-chloroperoxybenzoic acid (0.08 g) was added and after 30 minutes sodium hydrogen carbonate solution (50 ml) was added. The organic layer was separated, dried and volatile material was removed by evaporation. The residue was purified by chromatography on a Mega Bond Elut column (20 g) eluting with 10-80% EtOAc/isohexane to give the title compound (0.55 g) as a white foam. NMR: 1.19 (t, 3H), 1.62 (s, 3H), 3.14 (s, 3H), 3.52-3.60 (m, 2H), 8.00 (d, 1H), 8.14 (brs, 1H), 8.45-8.49 (m, 1H), 10.11 (brs, 1H); m/z: 420.

Workup

  1. additionwas added
  2. customThe organic layer was separated
  3. customdried
  4. customvolatile material was removed by evaporation
  5. customThe residue was purified by chromatography on a Mega Bond Elut column (20 g)
  6. washeluting with 10-80% EtOAc/isohexane

Sources & evidence

ORD record
ord-e9056a48fb5d48a38e3ecd18999b4c5e
Source dataset
uspto-grants-2004_02
Patent number
US06689909B1

Reaction notes

Loading…