Formic Acid → HCID 135850599, compound

HRID 2186763Notes

Reaction equation

HRID 2186763 reaction equation
C(O)=O.C([O:11][CH2:12][C:13]1[C:21]2[C:20](=[O:22])[NH:19][C:18]([C:23]3[C:24]([O:40][CH2:41][CH3:42])=[N:25][CH:26]=[C:27]([S:29]([N:32]4[CH2:37][CH2:36][N:35]([CH2:38][CH3:39])[CH2:34][CH2:33]4)(=[O:31])=[O:30])[CH:28]=3)=[N:17][C:16]=2[N:15]([CH2:43][CH3:44])[N:14]=1)C1C=CC=CC=1>[Pd].C(OCC)(=O)C>[CH2:41]([O:40][C:24]1[C:23]([C:18]2[NH:19][C:20](=[O:22])[C:21]3[C:13]([CH2:12][OH:11])=[N:14][N:15]([CH2:43][CH3:44])[C:16]=3[N:17]=2)=[CH:28][C:27]([S:29]([N:32]2[CH2:33][CH2:34][N:35]([CH2:38][CH3:39])[CH2:36][CH2:37]2)(=[O:31])=[O:30])=[CH:26][N:25]=1)[CH3:42]

Participants

5

Reactant 2

HCID 284Formic AcidHCID 135850605HCID 135850605, compound

Product 1

HCID 135850599HCID 135850599, compoundYield 58.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Formic acid (1.5 ml) was added to a mixture of the title compound of example 23 (750 mg, 1.3 mmol) and 10% palladium on charcoal (750 mg) in ethyl acetate (15 ml), and the reaction stirred under a nitrogen atmosphere at room temperature for 24 hours. The reaction mixture was filtered through Arbocel, the filter pad washed with water (30 ml) and ethyl acetate (30 ml), and the filtrate basified using 2N sodium hydroxide solution. The layers were separated, the aqueous extracted with dichloromethane (3×100 ml), and the combined organic solutions dried (MgSO4) and evaporated under reduced pressure. The residue was triturated with ether, to afford the title compound as a white solid, (375 mg).

Workup

  1. filtrationThe reaction mixture was filtered through Arbocel
  2. washthe filter pad washed with water (30 ml) and ethyl acetate (30 ml)
  3. customThe layers were separated
  4. extractionthe aqueous extracted with dichloromethane (3×100 ml)
  5. dry with materialthe combined organic solutions dried (MgSO4)
  6. customevaporated under reduced pressure
  7. customThe residue was triturated with ether

Sources & evidence

ORD record
ord-c060811d4f4f4965861e5f9d9e6e6dec
Source dataset
uspto-grants-2002_06
Patent number
US06407114B1

Reaction notes

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