HCID 58866156, compound → HCID 58866164, compound

HRID 1354288Notes

Reaction equation

HRID 1354288 reaction equation
C([O:8][NH:9][C:10]([C@H:12]1[C@@H:17]2[O:18][C:19]([CH3:22])([CH3:21])[O:20][C@@H:16]2[C@H:15]([OH:23])[CH2:14][N:13]1[S:24]([C:27]1[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=1)(=[O:26])=[O:25])=[O:11])C1C=CC=CC=1>C(OCC)(=O)C.[Pd]>[OH:8][NH:9][C:10]([C@H:12]1[C@@H:17]2[O:18][C:19]([CH3:21])([CH3:22])[O:20][C@@H:16]2[C@H:15]([OH:23])[CH2:14][N:13]1[S:24]([C:27]1[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=1)(=[O:26])=[O:25])=[O:11]

Participants

4

Reactant 1

HCID 58866156HCID 58866156, compound

Product 1

HCID 58866164HCID 58866164, compoundYield 90.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

The above compound (7) (278 mg) was dissolved in ethyl acetate (15 mL) and 10% Pd—C (38 mg) was added, and then the mixture was stirred under a hydrogen atmosphere room temperature for 2 hours. The catalyst was removed by filtration and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel medium pressure column chromatography (chloroform:methanol=50:1→30:1→10:1) and then freeze-dried to obtain the titled compound (205 mg) as a colorless amorphous.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe resulting residue was purified by silica gel medium pressure column chromatography (chloroform:methanol=50:1→30:1→10:1)
  4. customfreeze-dried

Sources & evidence

ORD record
ord-9574a07d434c41aabd85044de5c01062
Source dataset
uspto-grants-2007_05
Patent number
US07223779B2

Reaction notes

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