Oxygen → HCID 21892052, compound

HRID 28464Notes

Reaction equation

HRID 28464 reaction equation
[CH2:1]([C:4]1[C:9]2[O:10][C@@H:11]([CH2:14][O:15][S:16]([C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=3)(=[O:18])=[O:17])[CH2:12][O:13][C:8]=2[CH:7]=[CH:6][C:5]=1[N+:26]([O-:28])=[O:27])[CH:2]=C.[O:29]=[O+][O-].O=O.C(N(C(C)C)CC)(C)C>C(Cl)Cl>[CH3:25][C:22]1[CH:21]=[CH:20][C:19]([S:16]([O:15][CH2:14][CH:11]2[O:10][C:9]3[C:4]([CH2:1][CH:2]=[O:29])=[C:5]([N+:26]([O-:28])=[O:27])[CH:6]=[CH:7][C:8]=3[O:13][CH2:12]2)(=[O:17])=[O:18])=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 977OxygenHCID 24823OzoneHCID 81531DiisopropylethylamineHCID 12082206(R)-[8-allyl-7-nitro-2,3-dihydro-1,4-benzodioxin-2-yl]methyl4-methylbenzenesulfonate

Product 1

HCID 21892052HCID 21892052, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4.2 g (10 mmole) of toluene-4-sulfonic acid (2R)-8-allyl-7-nitro-2,3-dihydro-benzo(1,4)dioxin-2-ylmethyl ester in 400 mL of methylene chloride was cooled in a dry ice/isopropanol bath and saturated with ozone. It was then purged with oxygen and 2.6 g (20 mmole) of diisopropylethylamine added. The mixture was allowed to come to room temperature and stirred under nitrogen for 24 hours. It was then washed with 300 mL portions of 2 N HCl (aq), water and saturated brine, dried over magnesium sulfate, filtered and concentrated in vacuum to give 3.8 g of the (R)-enantiomer of the title compound as a white solid one-quarter hydrate, m.p. 116-120° C.

Workup

  1. additionadded
  2. customto come to room temperature
  3. washIt was then washed with 300 mL portions of 2 N HCl (aq), water and saturated brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-cfb4730cf9e0406fa149a7a8d266f8fc
Source dataset
uspto-grants-2008_09
Patent number
US07419986B2

Reaction notes

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