Ethyl Acetate → HCID 58981793, compound

HRID 1727913Notes

Reaction equation

HRID 1727913 reaction equation
C(OCC)(=O)C.[N:7]([CH2:10][CH2:11][O:12][CH2:13][C:14]1[NH:19][C:18]([CH3:20])=[C:17]([C:21]([OH:23])=[O:22])[CH:16]([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([Cl:30])[CH:25]=2)[C:15]=1[C:31](=[O:48])[NH:32][CH2:33][CH2:34][CH:35]([C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)=[N+]=[N-]>[H][H].[C].[Pd]>[NH2:7][CH2:10][CH2:11][O:12][CH2:13][C:14]1[N:19]=[C:18]([CH3:20])[C:17]([C:21]([OH:23])=[O:22])=[C:16]([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([Cl:30])[CH:25]=2)[C:15]=1[C:31](=[O:48])[NH:32][CH2:33][CH2:34][CH:35]([C:42]1[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=1)[C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1.[NH2:7][CH2:10][CH2:11][O:12][CH2:13][C:14]1[NH:19][C:18]([CH3:20])=[C:17]([C:21]([OH:23])=[O:22])[CH:16]([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([Cl:30])[CH:25]=2)[C:15]=1[C:31](=[O:48])[NH:32][CH2:33][CH2:34][CH:35]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1

Participants

6

Reactant 2

HCID 8857Ethyl AcetateHCID 86590785HCID 86590785, compound

Product 2

HCID 58981793HCID 58981793, compoundHCID 69069478HCID 69069478, compound

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 178418361HCID 178418361, compoundSolvent

Procedure

3 ml of ethyl acetate and 10% palladium carbon were added to 0.100 g (0.170 mmol) of 6-(2-azidoethoxy) methyl-4-(3-chlorophenyl)-5-(3,3-diphenylpropylcarbamoyl)-2-methyl-1,4-dihydropyridine-3-carboxylic acid and stirred at room temperature in hydrogen atmosphere under normal pressure for 40 hours. The reaction mixture was filtered and the filtrate was evaporated under reduced pressure. The residue thus obtained by evaporating the solvent was subjected to Reversed-phase High-performance Liquid Chromatography using octadodecyl group bounded type silica gel as a filler. Then, the obtained substance was eluted with the mixed solvent of water and acetonitrile. The fraction of the object compound was freeze-dried to obtain the title compound as a by-product material of 6-(2-aminoethoxy) methyl-4-(3-chlorophenyl)-5-(3,3-diphenylpropylcarbamoyl)-2-methyl-1,4-dihydropyridine-3-carboxylic acid.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe filtrate was evaporated under reduced pressure
  3. customThe residue thus obtained
  4. customby evaporating the solvent
  5. washThen, the obtained substance was eluted with the mixed solvent of water and acetonitrile
  6. customThe fraction of the object compound was freeze-dried

Sources & evidence

ORD record
ord-9a74018cbc8b43e6bd3b1ba49a11a1b7
Source dataset
uspto-grants-2009_02
Patent number
US07494989B2

Reaction notes

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