Ethanol → HCID 22100891, compound

HRID 1458357Notes

Reaction equation

HRID 1458357 reaction equation
C(OC(=O)[N:10]([CH2:21][CH2:22][C:23]1[C:31]2[C:26](=[CH:27][CH:28]=[C:29]([C:32]([C:35](=[O:45])[N:36]([CH2:41][CH2:42][CH2:43][CH3:44])[CH2:37][CH2:38][CH2:39][CH3:40])([CH3:34])[CH3:33])[CH:30]=2)[NH:25][C:24]=1[C:46]1[CH:51]=[C:50]([CH3:52])[CH:49]=[C:48]([CH3:53])[CH:47]=1)[CH2:11][CH2:12][CH2:13][CH2:14][C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1)C1C=CC=CC=1.CCO>[Pd].CCOC(C)=O>[CH3:53][C:48]1[CH:47]=[C:46]([C:24]2[NH:25][C:26]3[C:31]([C:23]=2[CH2:22][CH2:21][NH:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)=[CH:30][C:29]([C:32]([CH3:33])([CH3:34])[C:35]([N:36]([CH2:37][CH2:38][CH2:39][CH3:40])[CH2:41][CH2:42][CH2:43][CH3:44])=[O:45])=[CH:28][CH:27]=3)[CH:51]=[C:50]([CH3:52])[CH:49]=1

Participants

5

Reactant 2

HCID 702EthanolHCID 86753451HCID 86753451, compound

Product 1

HCID 22100891HCID 22100891, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 76.5 mg (0.105 mmol) of [2-[5-(1-dibutylcarbamoyl-1-methylethyl)-2-(3,5-dimethylphenyl)-1H-indol-3-yl]ethyl]-[4-(pyridin-3-yl)butyl]carbamic acid benzyl ester, 40 mg of 10% palladium on carbon, 4 ml of absolute EtOH, and 4 ml of EtOAc was shaken with H2 (approx. 47 psig) in a pressure vessel for 6 hours. The catalyst was removed by filtration through Celite under N2, and the filtrate was concentrated in vacuo at room temperature. The residue was purified by preparative TLC on 4 Analtech tapered silica gel plates (20×20 cm), which were developed in 92.5:7.5:0.75 CH2Cl2 -MeOH-concentrated NH4OH. The product band from each plate was isolated, combined, and extracted with 92.5:7.5:0.75 CH2Cl2 -MeOH-concentrated NH4OH. Concentration of the extracts in vacuo yielded 51.4 mg (82%) of a pale yellow, stiff gum; homogeneous by TLC in 92.5:7.5:0.75 CH2Cl2 -MeOH-concentrated NH40H. 500 MHz 1H NMR (CDCl3) was consistent with the assigned structure. Mass spectrum (ESI): m/e 595.6 (M+H)+.

Workup

  1. customThe catalyst was removed by filtration through Celite under N2
  2. concentrationthe filtrate was concentrated in vacuo at room temperature
  3. customThe residue was purified by preparative TLC on 4 Analtech tapered silica gel plates (20×20 cm), which
  4. customThe product band from each plate was isolated
  5. extractionextracted with 92.5:7.5:0.75 CH2Cl2 -MeOH-concentrated NH4OH
  6. customConcentration of the extracts in vacuo yielded 51.4 mg (82%) of a pale yellow, stiff gum
  7. concentrationhomogeneous by TLC in 92.5:7.5:0.75 CH2Cl2 -MeOH-concentrated NH40H

Sources & evidence

ORD record
ord-1f7fde026bd7458eb0650a18f28a4400
Source dataset
uspto-grants-1998_12
Patent number
US05849764

Reaction notes

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