HCID 19752584, compound → HCID 19752511, compound

HRID 483389Notes

Reaction equation

HRID 483389 reaction equation
[CH2:1]([N:8]([CH2:10][CH2:11][C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[C:18]([CH2:21][CH:22]3[C:26](=[O:27])[N:25]([CH2:28][C:29]4[CH:34]=[CH:33][CH:32]=[C:31]([C:35](=[O:38])[NH:36][CH3:37])[CH:30]=4)[C:24](=[O:39])[NH:23]3)[CH:19]=2)[NH:14][CH:13]=1)C)C1C=CC=CC=1>C(O)C.[Pd]>[CH3:1][NH:8][CH2:10][CH2:11][C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[C:18]([CH2:21][CH:22]3[C:26](=[O:27])[N:25]([CH2:28][C:29]4[CH:34]=[CH:33][CH:32]=[C:31]([C:35]([NH:36][CH3:37])=[O:38])[CH:30]=4)[C:24](=[O:39])[NH:23]3)[CH:19]=2)[NH:14][CH:13]=1

Participants

4

Reactant 1

HCID 19752584HCID 19752584, compound

Product 1

HCID 19752511HCID 19752511, compoundYield 40.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of the product from step (b) (257 mg) and 10% Pd/C (110 mg) in ethanol (16 ml) was hydrogenated at room temperature and atmospheric pressure for 6 hours (uptake 12 ml). The mixture was filtered through celite, the residue washed with ethanol and the filtrate evaporated in vacuo to give a colourless oil which was flash chromatographed through a silica column using DCM/ethanol/ammonia (50:8:1 v/v/v) to give the desired product as a colourless oil (87 mg).

Workup

  1. customwas hydrogenated at room temperature
  2. filtrationThe mixture was filtered through celite
  3. washthe residue washed with ethanol
  4. customthe filtrate evaporated in vacuo
  5. customto give a colourless oil which
  6. customchromatographed through a silica column

Sources & evidence

ORD record
ord-5133f00974ff441caa1ce14febf76e24
Source dataset
uspto-grants-1993_07
Patent number
US05225431

Reaction notes

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