HCID 15229847, compound → HCID 15229845, compound

HRID 1653666Notes

Reaction equation

HRID 1653666 reaction equation
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][N:2]1[CH:11]1[CH2:16][CH2:15][C:14]2([CH:21]=[CH:20][C:19]3[CH:22]=[C:23]([NH:26][S:27]([CH3:30])(=[O:29])=[O:28])[CH:24]=[CH:25][C:18]=3[O:17]2)[CH2:13][CH2:12]1>C(O)C.[Pd]>[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][N:2]1[CH:11]1[CH2:16][CH2:15][C:14]2([CH2:21][CH2:20][C:19]3[CH:22]=[C:23]([NH:26][S:27]([CH3:30])(=[O:28])=[O:29])[CH:24]=[CH:25][C:18]=3[O:17]2)[CH2:13][CH2:12]1

Participants

4

Reactant 1

HCID 15229847HCID 15229847, compound

Product 1

HCID 15229845HCID 15229845, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a stirred suspension of 5% Pd/C (10 wt. %, 1.7 mg) in ethanol (25 ml ) was added the olefin from step A above. The system was evacuated and purged with hydrogen twice and the reaciton mixture stirred at r.t. under 1 atm. of hydrogen. After three hours another portion of Pd/C (20 wt.%, 3.4 mg) was added and the reaction stirred overnight at r.t. It was then filtered through celite, the pad rinsed with ethanol and evaporated under reduced pressure. The resulting oil was chromatographed over silica gel with eluting with 5% MeOH:CHCl3. The pure material was recrystallized from EtOH to give 100 mg of off white crystals. 60.1%. mp 183°-185 ° C. 1H NMR (CDC13)δ7.11-6.79 (m, 8H), 4.14 (s,2H), 2.93 (s, 5H), 2.91 (s, 2H), 2.76 (t, J=7 Hz, 2H), 2.66-2.54 (m, 1H), 2.00 (d, J=9 Hz, 2H), 1.90-1.72 (m, 6H), 1.46-1.20 (m, 2H) Anal. Calcd for C24H30N2O3S.0.15H2O: C, 67.14; H, 7.11; N, 6.53. Found: C, 67.17; H, 6.99; N, 6.45. ##STR10##

Workup

  1. customThe system was evacuated
  2. custompurged with hydrogen twice
  3. additionAfter three hours another portion of Pd/C (20 wt.%, 3.4 mg) was added
  4. stirringthe reaction stirred overnight at r.t
  5. filtrationIt was then filtered through celite
  6. washthe pad rinsed with ethanol
  7. customevaporated under reduced pressure
  8. customThe resulting oil was chromatographed over silica gel
  9. washwith eluting with 5% MeOH
  10. customThe pure material was recrystallized from EtOH
  11. customto give 100 mg of off white crystals

Sources & evidence

ORD record
ord-a9b2928bbdee433e966d46ff41755f1a
Source dataset
uspto-grants-1995_04
Patent number
US05403846

Reaction notes

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