HCID 131723892, compound → HCID 131723890, compound

HRID 412864Notes

Reaction equation

HRID 412864 reaction equation
[Na:1].[Na].[C:3]([NH:6][C@@H:7]1[C@@H:12]([O:13]CC2C=CC=CC=2)[C@H:11]([O:21]CC2C=CC=CC=2)[C@@H:10]([CH2:29][O:30][S:31]([OH:34])(=[O:33])=[O:32])[O:9][C@H:8]1[O:35][C@H:36]1[C@@H:50]([O:51]CC2C=CC=CC=2)[C@@H:49]([CH2:59][O:60][S:61]([OH:64])(=[O:63])=[O:62])[O:48][C@@H:38]([O:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47])[C@@H:37]1[O:65]CC1C=CC=CC=1)(=[O:5])[CH3:4].[H][H]>CO.O.[OH-].[OH-].[Pd+2]>[Na:1].[Na:1].[C:3]([NH:6][C@@H:7]1[C@@H:12]([OH:13])[C@H:11]([OH:21])[C@@H:10]([CH2:29][O:30][S:31]([OH:34])(=[O:33])=[O:32])[O:9][C@H:8]1[O:35][C@H:36]1[C@@H:50]([OH:51])[C@@H:49]([CH2:59][O:60][S:61]([OH:64])(=[O:63])=[O:62])[O:48][C@@H:38]([O:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47])[C@@H:37]1[OH:65])(=[O:5])[CH3:4]

Participants

6

Reactant 2

HCID 131723892HCID 131723892, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 131723890HCID 131723890, compoundYield 180.6%

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Compound 21 (170 mg, 0.160 mmol) was dissolved in a mixture of methanol and water (3:1, 15 mL) and palladium hydroxide/carbon (180 mg) was added thereto. Inside of the reaction system was replaced with hydrogen gas, and catalytic reduction was performed at room temperature for 4 hours. The reaction mixture was filtered through Celite, and the filtrate was evaporated. The residue was purified with a column of Sephadex LH-20 (CHCl3:MeOH:H2O=5:10:3), further purified with a column of Dowex-50 (Na+) type (CHCl3:MeOH:H2O=1:3:1), and finally purified with a column of Sephadex LH-20 (CHCl3:MeOH:H2O=5:10:3) again to obtain Compound 22 (101.4 mg, 90.6%).

Workup

  1. additionwas added
  2. filtrationThe reaction mixture was filtered through Celite
  3. customthe filtrate was evaporated
  4. customThe residue was purified with a column of Sephadex
  5. custom(CHCl3:MeOH:H2O=5:10:3), further purified with a column of Dowex-50 (Na+) type (CHCl3:MeOH:H2O=1:3:1)
  6. customfinally purified with a column of Sephadex

Sources & evidence

ORD record
ord-4f867d90dd9c49fcb3b40fedd8338909
Source dataset
uspto-grants-2003_05
Patent number
US06562954B1

Reaction notes

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