Ozone → HCID 178473976, compound

HRID 1682123Notes

Reaction equation

HRID 1682123 reaction equation
[O:1]=[O+][O-].C1(C=[CH:11][C@@H:12]2[N:15]([C:16](=[O:18])[CH3:17])[C:14](=[O:19])[C@H:13]2[CH2:20][CH2:21][CH2:22][NH:23][C:24]([NH:36][C:37]([O:39][CH2:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)=[O:38])=[N:25][C:26]([O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[O:27])C=CC=CC=1>C(Cl)Cl>[CH:11]([C@@H:12]1[N:15]([C:16](=[O:18])[CH3:17])[C:14](=[O:19])[C@H:13]1[CH2:20][CH2:21][CH2:22][NH:23][C:24]([NH:36][C:37]([O:39][CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)=[O:38])=[N:25][C:26]([O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:27])=[O:1]

Participants

4

Reactant 2

HCID 24823OzoneHCID 178473975HCID 178473975, compound

Product 1

HCID 178473976HCID 178473976, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ozone was passed through a -78° C. methylene chloride solution of compound 27 (0.7 g, 1.2 mmol) until a blue color was maintained. Excess ozone was removed by purging the solution with N2. Dimethyl sulfide (1 mL) was added. The solution was warmed to room temperature, allowed to stand for 72 h, and concentrated. The residue was purified by silica gel chromatography (EtOAc:Et2O/1:3) to afford 230 mg (38%) of the title product.

Workup

  1. customwas passed through a -78° C.
  2. temperaturewas maintained
  3. customExcess ozone was removed
  4. customby purging the solution with N2
  5. additionDimethyl sulfide (1 mL) was added
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography (EtOAc:Et2O/1:3)

Sources & evidence

ORD record
ord-3b019f33618943eb8035fcb9c4a4e3ad
Source dataset
uspto-grants-1992_12
Patent number
US05175283

Reaction notes

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