HCID 67409087, compound → HCID 67409436, compound

HRID 1949655Notes

Reaction equation

HRID 1949655 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]([O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])[CH2:10][CH:9]1[CH:21]([C:26]1[C:34]2[C:29](=[CH:30][C:31]([F:35])=[CH:32][CH:33]=2)[NH:28][CH:27]=1)[CH2:22][N+:23]([O-])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CCO.[Ni]>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]([O:13][Si:14]([C:17]([CH3:19])([CH3:18])[CH3:20])([CH3:16])[CH3:15])[CH2:10][CH:9]1[CH:21]([C:26]1[C:34]2[C:29](=[CH:30][C:31]([F:35])=[CH:32][CH:33]=2)[NH:28][CH:27]=1)[CH2:22][NH2:23])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 1

HCID 67409087HCID 67409087, compound

Product 1

HCID 67409436HCID 67409436, compoundYield 97.3%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

To a solution of 78 (10.1 g, 20.0 mmol) in EtOH (150 mL) in a Parr bottle was added an aqueous suspension of Raney Ni (6 pipettes). The bottle was evacuated and flushed with H2 five times, charged to 50 PSI H2 (344.7 KPa) and shaken for 2.5 h. The reaction mixture was filtered through diatomaceous earth (Celite®) and concentrated to afford 79 (9.3 g, 97%) as an off-white powder which was used without further purification. Mass spectrum, m/z [478.2] (M+H)+.

Workup

  1. customThe bottle was evacuated
  2. customflushed with H2 five times
  3. additioncharged to 50 PSI H2 (344.7 KPa)
  4. filtrationThe reaction mixture was filtered through diatomaceous earth (Celite®)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-f5e380597db749229068d8d693c387c0
Source dataset
uspto-grants-2013_03
Patent number
US08399683B2

Reaction notes

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