m-Chloroperbenzoic acid → HCID 59210625, compound

HRID 2243304Notes

Reaction equation

HRID 2243304 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[CH:12]1([C:18]2[CH:53]=[CH:52][C:21]([CH2:22][O:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[CH2:30][CH2:31][CH:32]([S:41][C:42]3[CH:51]=[CH:50][C:45]([C:46]([O:48][CH3:49])=[O:47])=[CH:44][CH:43]=3)[CH2:33][CH2:34][CH2:35][CH2:36][C:37]([O:39][CH3:40])=[O:38])=[CH:20][CH:19]=2)[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1>C(Cl)Cl>[CH:12]1([C:18]2[CH:53]=[CH:52][C:21]([CH2:22][O:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[CH2:30][CH2:31][CH:32]([S:41]([C:42]3[CH:51]=[CH:50][C:45]([C:46]([O:48][CH3:49])=[O:47])=[CH:44][CH:43]=3)=[O:9])[CH2:33][CH2:34][CH2:35][CH2:36][C:37]([O:39][CH3:40])=[O:38])=[CH:20][CH:19]=2)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 59210559Methyl 4-{[1-(2-{2-[(4-cyclohexylbenzyl)oxy]phenyl}-ethyl)-6-methoxy-6-oxohexyl]sulfanyl}benzoate

Product 1

HCID 59210625HCID 59210625, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

At 0° C., 47 mg (0.19 mmol) of metachloroperbenzoic acid were added to a solution of 113 mg (0.19 mmol) of methyl 4-{[1-(2-{2-[(4-cyclohexylbenzyl)oxy]phenyl}-ethyl)-6-methoxy-6-oxohexyl]sulfanyl}benzoate 187 in 25 ml of CH2Cl2. The mixture was stirred at 0° C. for 30 min, and the cooling bath was then removed and stirring, was continued at room temperature for 16 h. After the reaction had ended, the mixture was washed successively with saturated Na2SO3 solution, saturated Na2CO3 solution, saturated NaCl solution and water. The organic phases were dried over Na2SO4 and the solvent was removed. The product was purified chromatographically (silica gel, cyclohexane/ethyl acetate 2:1)

Workup

  1. customthe cooling bath was then removed
  2. stirringstirring
  3. waitwas continued at room temperature for 16 h
  4. washthe mixture was washed successively with saturated Na2SO3 solution, saturated Na2CO3 solution, saturated NaCl solution and water
  5. dry with materialThe organic phases were dried over Na2SO4
  6. customthe solvent was removed
  7. customThe product was purified chromatographically (silica gel, cyclohexane/ethyl acetate 2:1)

Sources & evidence

ORD record
ord-336ac58ca36342a6a4074c482a72fe85
Source dataset
uspto-grants-2010_03
Patent number
US07674825B2

Reaction notes

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