HCID 23598865, compound → HCID 69583821, compound

HRID 891005Notes

Reaction equation

HRID 891005 reaction equation
C([O:8][CH2:9][N:10]1[C:21](=[O:22])[C:20]2[C:12](=[C:13]3[C:17](=[C:18]4[N:25]([C@@H:26]5[O:43][C@H:42]([CH2:44][O:45][C:46](=[O:48])[CH3:47])[C@@H:37]([O:38][C:39](=[O:41])[CH3:40])[C@H:32]([O:33][C:34](=[O:36])[CH3:35])[C@H:27]5[O:28][C:29](=[O:31])[CH3:30])[C:24]5[N:49]=[CH:50][CH:51]=[CH:52][C:23]=5[C:19]4=2)[NH:16][C:15]2[N:53]=[CH:54][CH:55]=[CH:56][C:14]3=2)[C:11]1=[O:57])C1C=CC=CC=1>CO.C(OCC)(=O)C.[Pd]>[OH:8][CH2:9][N:10]1[C:21](=[O:22])[C:20]2[C:12](=[C:13]3[C:17](=[C:18]4[N:25]([C@@H:26]5[O:43][C@H:42]([CH2:44][O:45][C:46](=[O:48])[CH3:47])[C@@H:37]([O:38][C:39](=[O:41])[CH3:40])[C@H:32]([O:33][C:34](=[O:36])[CH3:35])[C@H:27]5[O:28][C:29](=[O:31])[CH3:30])[C:24]5[N:49]=[CH:50][CH:51]=[CH:52][C:23]=5[C:19]4=2)[NH:16][C:15]2[N:53]=[CH:54][CH:55]=[CH:56][C:14]3=2)[C:11]1=[O:57]

Participants

5

Reactant 1

HCID 23598865HCID 23598865, compound

Product 1

HCID 69583821HCID 69583821, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the compound of Example 10c (0.090 mmol) in 4.5 ml of dry methanol and 1.5 ml of dry ethyl acetate there is added 10% palladium-on-carbon (84.0 mg). The reaction mixture is degassed twice and is then stirred at ambient temperature under a hydrogen atmosphere (1 bar) for 24 hours. After 24 hours, more 10% palladium-on-carbon (42.0 mg) is added. The reaction mixture is degassed again and is then held under a hydrogen atmosphere for 24 hours. The mixture is filtered over Celite, and the solid is washed with methanol and with chloroform. After evaporating off the solvents and purifying the residue by chromatography on silica gel (cyclohexane/ethyl acetate: 3/2), the expected product is isolated.

Workup

  1. customThe reaction mixture is degassed twice
  2. waitAfter 24 hours
  3. additionmore 10% palladium-on-carbon (42.0 mg) is added
  4. customThe reaction mixture is degassed again
  5. waitis then held under a hydrogen atmosphere for 24 hours
  6. filtrationThe mixture is filtered over Celite
  7. washthe solid is washed with methanol and with chloroform
  8. customAfter evaporating off the solvents
  9. custompurifying the residue by chromatography on silica gel (cyclohexane/ethyl acetate: 3/2)

Sources & evidence

ORD record
ord-79306c47420f4f3db143e0ea25c43e5b
Source dataset
uspto-grants-2006_02
Patent number
US07001906B2

Reaction notes

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