m-Chloroperbenzoic acid → HCID 11245695, compound

HRID 2233054Notes

Reaction equation

HRID 2233054 reaction equation
[OH:1][CH2:2][CH2:3][S:4][CH2:5][C:6]1[N:7]([CH3:25])[C:8](=[O:24])[C:9]2[C:14]([C:15]=1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[CH:13][C:12]([O:22][CH3:23])=[CH:11][CH:10]=2.ClC1C=CC=C(C(OO)=[O:34])C=1>ClCCl>[OH:1][CH2:2][CH2:3][S:4]([CH2:5][C:6]1[N:7]([CH3:25])[C:8](=[O:24])[C:9]2[C:14]([C:15]=1[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)=[CH:13][C:12]([O:22][CH3:23])=[CH:11][CH:10]=2)=[O:34]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 11382698HCID 11382698, compound

Product 1

HCID 11245695HCID 11245695, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-{[(2-hydroxyethyl)thio]methyl}-6-methoxy-2-methyl-4-phenylisoquinolin-1(2H)-one (31 mg, 0.087 mmol) in 2 mL of dichloromethane was added at 0° C. meta-chloroperbenzoic acid (16 mg, 0.091 mmol). After 15 minutes, the reaction mixture was partitioned between EtOAc and 2M Na2S2O3 solution, and the organic layer was washed with saturated NaHCO3 solution and brine, dried over Na2SO4, filtered, and concentrated in vacuo. The crude residue was purified by preparative reversed phase HPLC to provide the titled product. 1H-NMR (500 MHz, CDCl3) δ 8.43 (d, J=9.0 Hz, 1H), 7.44-7.55 (m, 3H), 7.33 (br d, J=8 Hz, 2H), 7.06 (dd, J=8.8, 2.4 Hz, 1H), 6.33 (d, J=2.4 Hz, 1H), 4.28 (d, J=13.9 Hz, 1H), 3.98 (d, J=13.9 Hz, 1H), 3.96-4.04 (m, 2H), 3.84, (s, 3H), 3.68 (s, 3H), 2.85 (m, 1H), 2.70 (m, 1H), ppm. ESI+ MS: 372.19 [M+H]+.

Workup

  1. customthe reaction mixture was partitioned between EtOAc and 2M Na2S2O3 solution
  2. washthe organic layer was washed with saturated NaHCO3 solution and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude residue was purified by preparative reversed phase HPLC

Sources & evidence

ORD record
ord-ee15f29f12c7492fac21a38c1e33162b
Source dataset
uspto-grants-2010_05
Patent number
US07709476B2

Reaction notes

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