Hydrogen Peroxide → HCID 59431064, compound

HRID 2204048Notes

Reaction equation

HRID 2204048 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[C@H:13]([OH:14])[C@@H:12]([OH:15])[C@H:11]([OH:16])[C@@H:10]([S:17][CH2:18][CH3:19])[O:9]2)=[CH:4][C:3]=1[CH2:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][CH2:28][CH3:29])=[CH:23][CH:22]=1.[OH:30]O>CC(O)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[C@H:13]([OH:14])[C@@H:12]([OH:15])[C@H:11]([OH:16])[C@@H:10]([S:17]([CH2:18][CH3:19])=[O:30])[O:9]2)=[CH:4][C:3]=1[CH2:20][C:21]1[CH:22]=[CH:23][C:24]([O:27][CH2:28][CH3:29])=[CH:25][CH:26]=1

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 24831713HCID 24831713, compound

Product 1

HCID 59431064HCID 59431064, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of compound from step A (10 mg, 0.023 mmol) in AcOH (0.5 ml) was added H2O2 (35 wt % solution in H2O, 3 mg, 0.092 mmol, 9 μl). The mixture was stirred at ambient temperature for 2 hours before being concentrated under vacuum. Purification of the mixture by silica gel chromatography (5% MeOH/CH2Cl2) afforded (2S,3R,4R,5S,6R)-2-[4-chloro-3-(4-ethoxy-benzyl)-phenyl]-6-ethanesulfinyl-tetrahydro-pyran-3,4,5-triol (as a mixture of diastereomers at sulfur) (2 mg, 19%) and (2S,3R,4R,5S,6R)-2-[4-Chloro-3-(4-ethoxy-benzyl)-phenyl]-6-ethanesulfonyl-tetrahydro-pyran-3,4,5-triol (5 mg, 46%) both as white solids.

Workup

  1. concentrationbefore being concentrated under vacuum
  2. customPurification of the mixture by silica gel chromatography (5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-357ca5778f5646778621be1c3a635309
Source dataset
uspto-grants-2016_06
Patent number
US09365602B2

Reaction notes

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