HCID 5479375, compound → HCID 5479357, compound

HRID 1613122Notes

Reaction equation

HRID 1613122 reaction equation
[OH:1][C@@H:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C@@H:3]1[NH:11][C:12](=[O:48])[C@H:13]([CH2:33][C:34]1[CH:39]=[CH:38][C:37]([O:40]CC2C=CC=CC=2)=[CH:36][CH:35]=1)[CH2:14][C@H:15]([OH:32])[C@@H:16]([NH:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CO.C1COCC1.[Pd]>[OH:1][C@@H:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C@@H:3]1[NH:11][C:12](=[O:48])[C@H:13]([CH2:33][C:34]1[CH:39]=[CH:38][C:37]([OH:40])=[CH:36][CH:35]=1)[CH2:14][C@H:15]([OH:32])[C@@H:16]([NH:24][C:25]([O:27][C:28]([CH3:30])([CH3:31])[CH3:29])=[O:26])[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 1

HCID 5479375HCID 5479375, compound

Product 1

HCID 5479357HCID 5479357, compoundYield 98%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

The product of Step J, 85 mg was dissolved in 10 mL of methanol and 10 mL of THF, and to it was added 0.10 g of 10% palladium on carbon. The mixture was stirred under an atmosphere of hydrogen for 48 hours at room temperature, then filtered and concentrated to dryness. The residue was dissolved in 10 mL of hot ethanol and 20 mL water was added. On cooling the white solid precipitate was collected and dried under vacuum over P2O5. The yield was 72 mg (98% yield) of pure product: mp 218°-219° C. (effervesces, sinters at 215) elemental analysis, Calc'd for C33H40N2O6 : (560.696): C, 70.69; H, 7.19; N, 5.00; Found: C, 70.62; H, 7.39; N, 4.79.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated to dryness
  3. dissolutionThe residue was dissolved in 10 mL of hot ethanol
  4. addition20 mL water was added
  5. temperatureOn cooling the white solid precipitate
  6. customwas collected
  7. dry with materialdried under vacuum over P2O5

Sources & evidence

ORD record
ord-cfbf927008ac4dec88cd04340309328f
Source dataset
uspto-grants-1993_03
Patent number
US05192668

Reaction notes

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