HCID 86750501, compound → HCID 86750500, compound

HRID 976104Notes

Reaction equation

HRID 976104 reaction equation
[C:1]1([N:7]([C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)[C:8]([N:10]2[CH2:15][CH2:14][C@@H:13]([C:16]([N:18]([CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[O:17])[CH2:12][C@@H:11]2[C:29]([NH:31][CH2:32][CH2:33][N:34](C(OCC2C=CC=CC=2)=O)[CH2:35][C:36]([NH2:38])=[O:37])=[O:30])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C(O)C.[Pd]>[C:49]1([N:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:8]([N:10]2[CH2:15][CH2:14][C@@H:13]([C:16]([N:18]([CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[O:17])[CH2:12][C@@H:11]2[C:29]([NH:31][CH2:32][CH2:33][NH:34][CH2:35][C:36]([NH2:38])=[O:37])=[O:30])=[O:9])[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1

Participants

4

Reactant 1

HCID 86750501HCID 86750501, compound

Product 1

HCID 86750500HCID 86750500, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 0.055 g (0.074 mmole) of trans 1-(N,N-diphenylaminocarbonyl)-2-(RS)-(2-(N-(benzyloxycarbonyl)-N-(aminocarbonylmethyl)amino)ethylaminocarbonyl)-4-(RS)-(N,N-dipentylaminocarbonyl)piperidine (prepared in Example 3, Step D above) in 5 mL of ethanol was treated with 32 mg of 10% palladium on carbon and the resulting slurry was then stirred under an atmosphere of hydrogen for 3 hr. The mixture was then filtered through a cake of Celite, the cake was washed with 100 mL of ethanol, and the filtrate was concentrated in vacuo, to give 39 mg (87%) of an oil.

Workup

  1. filtrationThe mixture was then filtered through a cake of Celite
  2. washthe cake was washed with 100 mL of ethanol
  3. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-59099a0774bd46f8ad2dc0049b5607ab
Source dataset
uspto-grants-1997_03
Patent number
US05610165

Reaction notes

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