Formaldehyde → HCID 22325568, compound

HRID 496313Notes

Reaction equation

HRID 496313 reaction equation
[CH3:1][N:2]1[C:7](=[O:8])[C:6]2[CH:9]=[C:10]([C:12]3[CH:17]=[C:16]([S:18]([N:21]4[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]4)(=[O:20])=[O:19])[CH:15]=[CH:14][C:13]=3[O:27][CH2:28][CH2:29][CH3:30])[NH:11][C:5]=2[N:4]([CH2:31][CH2:32][CH3:33])[C:3]1=[O:34].[CH2:35]=O>[Pd]>[CH3:1][N:2]1[C:7](=[O:8])[C:6]2[CH:9]=[C:10]([C:12]3[CH:17]=[C:16]([S:18]([N:21]4[CH2:26][CH2:25][N:24]([CH3:35])[CH2:23][CH2:22]4)(=[O:20])=[O:19])[CH:15]=[CH:14][C:13]=3[O:27][CH2:28][CH2:29][CH3:30])[NH:11][C:5]=2[N:4]([CH2:31][CH2:32][CH3:33])[C:3]1=[O:34]

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 22325564HCID 22325564, compound

Product 1

HCID 22325568HCID 22325568, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A mixture of the title compound of Example 87 (0.4 g, 0.82 mmol), formaldehyde (0.14 mL, 37% in water, 1.63 mmol) and palladium 10% on activated carbon (40 mg) was hydrogenated for 2 h. The catalyst was removed by filtration through celite and the filtrate was evaporated under reduced pressure. The resulting crude product was purified by flash column chromatography on silica-gel (dichloromethane-ethanol-ammonium hydroxide 180:8:1) to yield the title compound (0.07 g, 17%) as an off-white solid.

Workup

  1. customThe catalyst was removed by filtration through celite
  2. customthe filtrate was evaporated under reduced pressure
  3. customThe resulting crude product was purified by flash column chromatography on silica-gel (dichloromethane-ethanol-ammonium hydroxide 180:8:1)

Sources & evidence

ORD record
ord-329c5d5eb3a1450aa12fbbb8d8df686a
Source dataset
uspto-grants-2005_09
Patent number
US06943253B2

Reaction notes

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