Ozone → HCID 178455000, compound

HRID 1195148Notes

Reaction equation

HRID 1195148 reaction equation
[O:1]=[O+][O-].C1(C=[CH:11][C@H:12]2[N:15]([Si:16]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17])[C:14](=[O:23])[C@H:13]2[CH2:24][CH2:25][CH2:26][NH:27][C:28]([NH:40][C:41]([O:43][CH2:44][C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)=[O:42])=[N:29][C:30]([O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[O:31])C=CC=CC=1>C(Cl)Cl>[CH:11]([C@H:12]1[N:15]([Si:16]([C:19]([CH3:20])([CH3:22])[CH3:21])([CH3:17])[CH3:18])[C:14](=[O:23])[C@H:13]1[CH2:24][CH2:25][CH2:26][NH:27][C:28]([NH:40][C:41]([O:43][CH2:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)=[O:42])=[N:29][C:30]([O:32][CH2:33][C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1)=[O:31])=[O:1]

Participants

4

Reactant 2

HCID 24823OzoneHCID 178454998HCID 178454998, compound

Product 1

HCID 178455000HCID 178455000, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ozone was passed through a -78° C. methylene chloride (100 mL) solution of compound 4b (4.73 g, 7.22 mmol) until a blue color was maintained. Excess ozone was purged with nitrogen. Dimethyl sulfide (10 mL) was added. The solution was allowed to stand for 16 h and concentrated to afford the title product which was not further purified but used directly in Step B.

Workup

  1. customwas passed through a -78° C.
  2. temperaturewas maintained
  3. customExcess ozone was purged with nitrogen
  4. additionDimethyl sulfide (10 mL) was added
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-307170d0642b4fa9ae8746cbe87bcd58
Source dataset
uspto-grants-1992_05
Patent number
US05110812

Reaction notes

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