Benzoylacetone → HCID 68418820, compound

HRID 271853Notes

Reaction equation

HRID 271853 reaction equation
[NH2:1][C@@H:2]([CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][NH:21][CH2:22][C:23](=[O:30])[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH:15]=2)=[CH:10][CH:9]=1)[C:3]([O:5][CH3:6])=[O:4].[C:31]([CH2:39][C:40](=O)[CH3:41])(=[O:38])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>CO>[C:23]([CH2:22][NH:21][CH2:20][C:16]1[CH:15]=[C:14]([C:11]2[CH:10]=[CH:9][C:8]([CH2:7][C@H:2]([NH:1][C:40]([CH3:41])=[CH:39][C:31](=[O:38])[C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[C:3]([O:5][CH3:6])=[O:4])=[CH:13][CH:12]=2)[CH:19]=[CH:18][CH:17]=1)(=[O:30])[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

4

Reactant 2

HCID 7166BenzoylacetoneHCID 86601621HCID 86601621, compound

Product 1

HCID 68418820HCID 68418820, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 0.65 g (1.62 mmol) of methyl (S)-2-amino-3-{3′-[(benzoylmethylamino)methyl]biphenyl-4-yl}propionate, 0.32 g (1.94 mmol) of benzoylacetone, 3 g of molecular sieve 4A are added to 15 ml of methanol. The reaction mixture is refluxed for 14 h and then filtered through Celite. After evaporation of the solvents, the residue is purified by chromatography on a column of silica and eluted with a 7/3 heptane/ethyl acetate mixture. 0.62 g of desired product is isolated with 70% yield.

Workup

  1. temperatureThe reaction mixture is refluxed for 14 h
  2. filtrationfiltered through Celite
  3. customAfter evaporation of the solvents
  4. customthe residue is purified by chromatography on a column of silica
  5. washeluted with a 7/3 heptane/ethyl acetate mixture

Sources & evidence

ORD record
ord-6418eb58926d418d9e60573c8e2dcfa9
Source dataset
uspto-grants-2008_11
Patent number
US07452878B2

Reaction notes

Loading…