m-Chloroperbenzoic acid → HCID 69748925, compound

HRID 2301022Notes

Reaction equation

HRID 2301022 reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[Cl:12][C:13]1[CH:18]=[C:17]([S:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[S:28][CH3:29])(=[O:21])=[O:20])[CH:16]=[CH:15][C:14]=1[NH:30][C:31](=[O:39])[C@:32]([OH:38])([CH3:37])[C:33]([F:36])([F:35])[F:34]>C(Cl)Cl>[Cl:12][C:13]1[CH:18]=[C:17]([S:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[S:28]([CH3:29])=[O:6])(=[O:20])=[O:21])[CH:16]=[CH:15][C:14]=1[NH:30][C:31](=[O:39])[C@:32]([OH:38])([CH3:37])[C:33]([F:35])([F:36])[F:34]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 11419637HCID 11419637, compound

Product 1

HCID 69748925HCID 69748925, compoundYield 65.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

m-Chloroperoxybenzoic acid (50%, 0.293 g) was added to a solution of (R)-N-[2-chloro-4-(2-methylsulphanylphenylsulphonyl)phenyl]-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide (Example 1) (0.384 g) in DCM (40 ml). The mixture was stirred at ambient temperature for 6 hours then washed with saturated aqueous sodium hydrogen carbonate solution (3×100 ml), water (100 ml) and brine and then dried. Volatile material was removed by evaporation and the residue was purified by chromatography on a silica gel Mega Bond Elut column eluting with 50-70% ethyl acetate/hexane to give the title compound (0.26 g) as a solid. Mp 118-120° C.; NMR (CDCl3): 1.70 (s, 3H), 3.0 (m, 3H), 4.85 (brs, 1H), 7.75 (t, 1H), 7.85 (m, 2H), 8.0 (m, 1H), 8.15 (d, 1H), 8.3 (d, 1H), 8.65 (dd, 1H), 9.40 (brs, 1H); MS (ESP−): 468; EA: found: C, 44.3; H, 3.7; N, 2.6%; C17H15ClF3NO5S2.0.125C4H8O2.0.3C4H10O requires: C, 44.64; H, 3.81; N, 2.78%.

Workup

  1. washthen washed with saturated aqueous sodium hydrogen carbonate solution (3×100 ml), water (100 ml) and brine
  2. customdried
  3. customVolatile material was removed by evaporation
  4. customthe residue was purified by chromatography on a silica gel Mega Bond Elut column
  5. washeluting with 50-70% ethyl acetate/hexane

Sources & evidence

ORD record
ord-cea2063811854408a76706084bb2b33a
Source dataset
uspto-grants-2002_12
Patent number
US06498275B1

Reaction notes

Loading…