Ammonium formate → HCID 57559184, compound

HRID 1723711Notes

Reaction equation

HRID 1723711 reaction equation
C([N:8]1[CH2:12][C@H:11]([N:13]2[CH2:18][CH2:17][CH2:16][CH2:15][C:14]2=[O:19])[C@@H:10]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH2:9]1)C1C=CC=CC=1.C([O-])=O.[NH4+]>CO.[Pd]>[O:19]=[C:14]1[CH2:15][CH2:16][CH2:17][CH2:18][N:13]1[C@H:11]1[CH2:12][NH:8][CH2:9][C@@H:10]1[NH:20][C:21](=[O:27])[O:22][C:23]([CH3:25])([CH3:24])[CH3:26]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 66605976HCID 66605976, compound

Product 1

HCID 57559184HCID 57559184, compoundYield 4,705.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of the product of Step 8 (2 g, 0.06 mmol) in MeOH was added excess ammonium formate and 10% Pd/C. The reaction mixture was heated under reflux overnight. After filtering, the solution was evaporated and residue was purified on silica gel (10% MeOH/chloroform) to obtain the title product (800 mg). 1H NMR (300 MHz, CDCl3) δ 5.25 (1H,s), 4.7 (1H, m), 3.45 (1H, m), 3.25 (1H, m), 3.04 (m) 2.9 (1H, m), 2.5 (6H, m), 1.80 (4H, m), 1.45 (9H, s). MS m/z 284 (MH+).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux overnight
  3. filtrationAfter filtering
  4. customthe solution was evaporated
  5. customresidue was purified on silica gel (10% MeOH/chloroform)

Sources & evidence

ORD record
ord-b249a093ecf247039111580620fc4d77
Source dataset
uspto-grants-2009_02
Patent number
US07485641B2

Reaction notes

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