m-Chloroperbenzoic acid → HCID 22458972, compound

HRID 2185052Notes

Reaction equation

HRID 2185052 reaction equation
[C:1]1([CH2:7][CH2:8][C:9]2[C:13]3[CH:14]=[CH:15][C:16]([OH:21])=[C:17]([CH2:18][CH2:19][CH3:20])[C:12]=3[S:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.ClC1C=CC=C(C(OO)=[O:30])C=1>C(Cl)Cl>[C:1]1([CH2:7][CH2:8][C:9]2[C:13]3[CH:14]=[CH:15][C:16]([OH:21])=[C:17]([CH2:18][CH2:19][CH3:20])[C:12]=3[S:11](=[O:30])[CH:10]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 22458983HCID 22458983, compound

Product 1

HCID 22458972HCID 22458972, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The product of Example 63, Step H (2.017 grams) in CH2Cl2 solution (40 mL) was stirred (0° C.) and treated with solid 75% m-chloroperbenzoic acid (1.567 grams) in portions. The reaction was warmed to ambient temperature after 15 minutes and stirred for 1.5 hours. Partition of the reaction between isopropyl acetate and aqueous sodium bicarbonate was followed by washing of the organic with aqueous sodium bicarbonate, then water. Drying over magnesium sulfate, filtration and evaporation afforded a solid which was chromatographed over silica gel (2 step gradient; 5:1 hex/ethyl acetate; 5:2 hex/ethyl acetate; 5:2:0.35 hex/ethyl acetate/methanol). The title compound was acquired as a white solid.

Workup

  1. customPartition of the reaction between isopropyl acetate and aqueous sodium bicarbonate
  2. washby washing of the organic with aqueous sodium bicarbonate
  3. dry with materialDrying over magnesium sulfate, filtration and evaporation
  4. customafforded a solid which
  5. customwas chromatographed over silica gel (2 step gradient; 5:1 hex/ethyl acetate; 5:2 hex/ethyl acetate; 5:2:0.35 hex/ethyl acetate/methanol)

Sources & evidence

ORD record
ord-2538711359134e0882bce42407511a99
Source dataset
uspto-grants-2002_06
Patent number
US06399640B1

Reaction notes

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