Ethyl 3-({[4-({[5-(benzyloxy)-3-methyl-1-benzofuran-2-yl](cyclohexyl)methyl}amino)phenyl]carbonyl}amino)propanoate → Ethyl 3-{[(4-{[cyclohexyl(5-hydroxy-3-methyl-1-benzofuran-2-yl)methyl]amino}phenyl)carbonyl]amino}propanoate

HRID 2091361Notes

Reaction equation

HRID 2091361 reaction equation
C([O:8][C:9]1[CH:10]=[CH:11][C:12]2[O:16][C:15]([CH:17]([NH:24][C:25]3[CH:30]=[CH:29][C:28]([C:31]([NH:33][CH2:34][CH2:35][C:36]([O:38][CH2:39][CH3:40])=[O:37])=[O:32])=[CH:27][CH:26]=3)[CH:18]3[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]3)=[C:14]([CH3:41])[C:13]=2[CH:42]=1)C1C=CC=CC=1>C(O)C.[Pt]=O>[CH:18]1([CH:17]([NH:24][C:25]2[CH:26]=[CH:27][C:28]([C:31]([NH:33][CH2:34][CH2:35][C:36]([O:38][CH2:39][CH3:40])=[O:37])=[O:32])=[CH:29][CH:30]=2)[C:15]2[O:16][C:12]3[CH:11]=[CH:10][C:9]([OH:8])=[CH:42][C:13]=3[C:14]=2[CH3:41])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

4

Reactant 1

HCID 66777551Ethyl 3-({[4-({[5-(benzyloxy)-3-methyl-1-benzofuran-2-yl](cyclohexyl)methyl}amino)phenyl]carbonyl}amino)propanoate

Product 1

HCID 66778243Ethyl 3-{[(4-{[cyclohexyl(5-hydroxy-3-methyl-1-benzofuran-2-yl)methyl]amino}phenyl)carbonyl]amino}propanoateYield 68%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Procedure

Ethyl 3-[{[4-({[5-(benzyloxy)-3-methyl-1-benzofuran-2-yl](cyclohexyl)methyl}amino)phenyl]carbonyl}amino]propanoate (5.6 g) synthesized in Example A158(1) was dissolved in ethanol (100 mL), and platinum oxide (0.50 g) was added to the solution. The reaction mixture was stirred under hydrogen atmosphere (1 atm) at room temperature overnight. The reaction mixture was filtered, and the residue was washed with ethanol. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:1, volume ratio) to give the title object compound (3.2 g, 68%) as a yellow oil.

Workup

  1. filtrationThe reaction mixture was filtered
  2. washthe residue was washed with ethanol
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:1, volume ratio)

Sources & evidence

ORD record
ord-17cfbf93aa004cac86ebbe10dc7743bf
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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