Methane → HCID 58505055, compound

HRID 1944928Notes

Reaction equation

HRID 1944928 reaction equation
[C:1]([O:5][C:6]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C@@H:20]([O:48][Si:49]([C:52]([CH3:55])([CH3:54])[CH3:53])([CH3:51])[CH3:50])[CH2:21][N:22]([CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][O:36][CH2:37][CH2:38][C:39]2[CH:44]=[CH:43][C:42]([N+:45]([O-])=O)=[CH:41][CH:40]=2)[C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[C:13]2[C:18]=1[NH:17][C:16](=[O:19])[CH:15]=[CH:14]2)=[O:7])([CH3:4])([CH3:3])[CH3:2].C.O.NN>CO.O.O.O.O.O.O.[Fe](Cl)(Cl)Cl>[NH2:45][C:42]1[CH:41]=[CH:40][C:39]([CH2:38][CH2:37][O:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][N:22]([CH2:21][C@@H:20]([C:12]2[CH:11]=[CH:10][C:9]([O:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])=[C:18]3[C:13]=2[CH:14]=[CH:15][C:16](=[O:19])[NH:17]3)[O:48][Si:49]([C:52]([CH3:55])([CH3:54])[CH3:53])([CH3:51])[CH3:50])[C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[CH:44][CH:43]=1

Participants

6

Reactant 3

HCID 297MethaneHCID 24654Hydrazine hydrate (1:1)HCID 58505091HCID 58505091, compound

Product 1

HCID 58505055HCID 58505055, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 16211236Trichloroiron;hexahydrateCatalystHCID 887MethanolSolvent

Procedure

A solution of Intermediate 110 (0.38 mmol) in methanol (9 mL) was treated with iron (III) chloride hexahydrate (10 mg) and decolorizing charcoal (100 mg). While the mixture was being heated to reflux, hydrazine monohydrate (1.0 mL) was added dropwise via syringe. After two hours of heating at reflux, the mixture was allowed to cool and was filtered through a pad of Celite diatomaceous earth. The filtrate was concentrated to dryness under reduced pressure and the residue was purified via automated flash silica gel chromatography, using a 12 g Silicycle SiliSep flash column (dichloromethane/methanol/ammonium hydroxide). Concentration of the desired fractions under reduced pressure provided the title compound (0.14 g, 56%) as a black foam. ES/MS calcd. for C36H56N3O6Si+ 654.4. Found m/z=654.5 (M+H)+.

Workup

  1. temperatureWhile the mixture was being heated
  2. temperatureto reflux
  3. temperatureAfter two hours of heating
  4. temperatureat reflux
  5. temperatureto cool
  6. filtrationwas filtered through a pad of Celite diatomaceous earth
  7. concentrationThe filtrate was concentrated to dryness under reduced pressure
  8. customthe residue was purified via automated flash silica gel chromatography

Sources & evidence

ORD record
ord-23424f96c7a0484b80fbd10db96b5642
Source dataset
uspto-grants-2013_03
Patent number
US08394829B2

Reaction notes

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