Ammonium formate → HCID 17894940, compound

HRID 727559Notes

Reaction equation

HRID 727559 reaction equation
C([O-])=O.[NH4+].C([O:12][NH:13][C:14](=[O:36])[CH2:15][C:16]1([CH2:32][CH:33]([CH3:35])[CH3:34])[C:20](=[O:21])[N:19]([CH2:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:18](=[O:30])[N:17]1[CH3:31])C1C=CC=CC=1>[Pd].CCO>[OH:12][NH:13][C:14](=[O:36])[CH2:15][C:16]1([CH2:32][CH:33]([CH3:34])[CH3:35])[C:20](=[O:21])[N:19]([CH2:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:18](=[O:30])[N:17]1[CH3:31]

Participants

5

Reactant 2

HCID 2723923Ammonium formate2×HCID 53999817HCID 53999817, compound

Product 1

HCID 17894940HCID 17894940, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Ammonium formate (59.0 mg, 0.936 mmol) is added to a mixture of N-benzyloxy-3-methyl-4-(2-methylpropyl)-2,5-dioxo-1-(2-phenylethyl)-4-imidazolidineacetamide (91.0 mg, 0.208 mmol), EtOH (2.5 mL), and 10% Pd/C (15 mg). The mixture is stirred at room temperature for 5.5 hours. Additional ammonium formate (35.0 mg, 0.555 mmol) is added after 2.5 hours. The mixture is filtered, the solids washed with MeOH (3×15 mL) and CHCl3 (3×15 mL), and the filtrate concentrated. The residue was taken up into CHCl3 (40 mL), dried (MgSO4), filtered, and concentrated to give 64.7 mg (90%) of the title compound as an oil. Crystallization from ether/hexane provided 46.4 mg (64%) of the title compound as a white powder (mp 127°-129° C.).

Workup

  1. filtrationThe mixture is filtered
  2. washthe solids washed with MeOH (3×15 mL) and CHCl3 (3×15 mL)
  3. concentrationthe filtrate concentrated
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-31eef79eb2b940a080cce9cfb0ed47b3
Source dataset
uspto-grants-1998_01
Patent number
US05712300

Reaction notes

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