HCID 131718536, compound → HCID 131718538, compound

HRID 1728651Notes

Reaction equation

HRID 1728651 reaction equation
[ClH:1].[CH2:2]1[O:32][C:31]2[CH:30]=[CH:29][C:6]([O:7][CH2:8][C@H:9]3[C@H:14]([C:15]4[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[CH:17][CH:16]=4)[CH2:13][CH2:12][N:11]([CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH2:10]3)=[CH:5][C:4]=2[O:3]1>C(O)C>[ClH:1].[NH2:21][C:18]1[CH:17]=[CH:16][C:15]([C@@H:14]2[CH2:13][CH2:12][N:11]([CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH2:10][C@H:9]2[CH2:8][O:7][C:6]2[CH:29]=[CH:30][C:31]3[O:32][CH2:2][O:3][C:4]=3[CH:5]=2)=[CH:20][CH:19]=1

Participants

3

Reactant 1

HCID 131718536HCID 131718536, compound

Product 1

HCID 131718538HCID 131718538, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Compound (7) (0.39 g) in abs. ethanol (50 ml) was hydrogenated at atm. pressure using 5% PdC (50 mg) as catalyst. The reaction mixture was filtered, evaporated to dryness. Extraction with NaOH(4N)-ether, separation of the etheral layer, drying (MgSO4), followed by evaporation to dryness gave an yellow oil which was purified on a silica gel column and precipitated as a very hygroscopic hydrochloride from acetone-ether. Identified by 1H NMR.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customevaporated to dryness
  3. extractionExtraction
  4. customwith NaOH(4N)-ether, separation of the etheral layer
  5. dry with materialdrying (MgSO4)
  6. customfollowed by evaporation to dryness
  7. customgave an yellow oil which
  8. customwas purified on a silica gel column
  9. customprecipitated as a very hygroscopic hydrochloride from acetone-ether

Sources & evidence

ORD record
ord-aa0d28631c9e404ba4d70bbd1ac1d4c3
Source dataset
uspto-grants-1994_07
Patent number
US05328917

Reaction notes

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