m-Chloroperbenzoic acid → HCID 59557716, compound

HRID 1175305Notes

Reaction equation

HRID 1175305 reaction equation
[CH2:1]([O:4][CH2:5][C:6]1[CH:11]=[C:10]([Cl:12])[C:9]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([CH2:20][CH3:21])=[CH:16][CH:15]=2)=[CH:8][C:7]=1[C@H:22]1[C@H:27]([OH:28])[C@@H:26]([OH:29])[C@H:25]([OH:30])[C@@H:24]([CH2:31][OH:32])[O:23]1)[CH:2]=[CH2:3].C1C=C(Cl)C=C(C(OO)=[O:41])C=1>C(Cl)Cl>[Cl:12][C:10]1[C:9]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([CH2:20][CH3:21])=[CH:16][CH:15]=2)=[CH:8][C:7]([C@H:22]2[C@H:27]([OH:28])[C@@H:26]([OH:29])[C@H:25]([OH:30])[C@@H:24]([CH2:31][OH:32])[O:23]2)=[C:6]([CH2:5][O:4][CH2:1][CH:2]2[CH2:3][O:41]2)[CH:11]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 25168565HCID 25168565, compound

Product 1

HCID 59557716HCID 59557716, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
40 °C

Procedure

To a solution of (2S,3R,4R,5S,6R)-2-(2-(allyloxymethyl)-4-chloro-5-(4-ethylbenzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol (463 mg, 1 mmol) in CH2Cl2 (2 mL) at 0° C., was added mCPBA (350 mg, 2 mmol). The mixture was heated to 40° C. and kept at that temperature overnight. Upon being cooled to room temperature, 10 mL of CH2Cl2 was added to dilute the solution. The solution was then washed with aqueous NaHCO3 and brine prior to drying over Na2SO4. The solvent was removed under reduced pressure and purification of the resulting mixture with preparative TLC gave two isomers with undetermined absolute configurations.

Workup

  1. customkept at that temperature overnight
  2. temperatureUpon being cooled to room temperature
  3. additionto dilute the solution
  4. washThe solution was then washed with aqueous NaHCO3 and brine
  5. dry with materialto drying over Na2SO4
  6. customThe solvent was removed under reduced pressure and purification of the resulting mixture with preparative TLC
  7. customgave two isomers with undetermined absolute configurations

Sources & evidence

ORD record
ord-9bb41e42d4f043d386c7636e054d7df8
Source dataset
uspto-grants-2010_11
Patent number
US07838498B2

Reaction notes

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