HCID 66777899, compound → HCID 66777718, compound

HRID 2091342Notes

Reaction equation

HRID 2091342 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]([N:33]([CH3:41])[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]([CH3:42])[C:13]=2[CH:43]=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]([N:33]([CH3:41])[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:43][C:13]=3[C:14]=2[CH3:42])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

4

Reactant 1

HCID 66777899HCID 66777899, compound

Product 1

HCID 66777718HCID 66777718, compoundYield 79%

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}(methyl)amino]-propanoate (2.46 g) synthesized in Example A154(2) was dissolved in ethanol (50 mL), and platinum oxide (0.33 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 (1.64 g, 79%) 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-2a38d9b362dc4cfb8ddff5fad45aa23e
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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