Ethanol → HCID 23574467, compound

HRID 2217152Notes

Reaction equation

HRID 2217152 reaction equation
CO[C:3](=[O:25])[C@@H:4]1[CH2:8][C@@H:7]([OH:9])[CH2:6][N:5]1[C:10](=[O:24])[C:11]1[CH:16]=[C:15]([O:17][CH3:18])[C:14](OC)=[CH:13][C:12]=1[N+:21]([O-])=O.C(Cl)(Cl)Cl.C[CH2:31][OH:32]>[Pd].Cl>[CH3:31][O:32][C:16]1[C:11]2[C:10](=[O:24])[N:5]3[CH2:6][C@H:7]([OH:9])[CH2:8][C@H:4]3[C:3](=[O:25])[NH:21][C:12]=2[CH:13]=[CH:14][C:15]=1[O:17][CH3:18]

Participants

6

Reactant 3

HCID 702EthanolHCID 6212ChloroformHCID 58658823HCID 58658823, compound

Product 1

HCID 23574467HCID 23574467, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 313Hydrochloric AcidSolvent

Procedure

10% Pd/C catalyst (3.3 g) was added to a solution of 3 (33.0 g, 93.1 mmol) in absolute EtOH (250 mL). The reaction mixture was hydrogenated under pressure using a Parr hydrogenator at 55 psi H2 for 18 hours. The reaction mixture was filtered through celite, and the celite washed with hot MeOH, taking care not to allow the filter cake to dry out. Removal of excess solvent afforded the crude product (20.14 g). The crude product was allowed to stir in 1 N HCl (200 mL) and CHCl3 (200 mL) for 30 minutes. The organic layer was washed with 1 N HCl (100 mL) and the aqueous layers were combined and neutralised with saturated aqueous NaHCO3. On leaving the aqueous extract overnight, a fine white precipitate formed (4) which was collected by filtration and dried (7.81 g, 26.72 mmol, 29%). 1H NMR (270 MHz, CDCl3) δ 10.06 (s, 1H, NH), 7.61 (s, 1H, ArH), 7.36 (s, 1H, ArH), 4.49-4.41 (m, 1H, 2), 4.22-4.17 (m, 1H, 11a), 3.88 (s, 6H), 3.82-3.55 (m, 2H, 3), 3.20 (br s, 1H, OH), 2.87-2.77 (m, 1H, 1), 2.10-2.05 (m, 1H, 1); 13C NMR (CDCl3) δ 170.2, 165.9, 152.0, 145.7, 130.7, 118.2, 111.9, 104.2, 68.1, 56.0, 55.6, 54.2, 34.6, 18.8.

Workup

  1. customfor 18 hours
  2. filtrationThe reaction mixture was filtered through celite
  3. washthe celite washed with hot MeOH
  4. customto dry out
  5. customRemoval of excess solvent
  6. customafforded the crude product (20.14 g)
  7. washThe organic layer was washed with 1 N HCl (100 mL)
  8. customOn leaving the
  9. extractionaqueous extract overnight

Sources & evidence

ORD record
ord-5a95ee2f563f40028eaa5db548ae1b0d
Source dataset
uspto-grants-2008_08
Patent number
US07407951B2

Reaction notes

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