HCID 86758971, compound → HCID 86758970, compound

HRID 412868Notes

Reaction equation

HRID 412868 reaction equation
[C:1]([NH:4][C@@H:5]1[C@@H:10]([O:11]CC2C=CC=CC=2)[C@H:9]([O:19]CC2C=CC=CC=2)[C@@H:8]([CH2:27][OH:28])[O:7][C@H:6]1[O:29][C@H:30]1[C@@H:63]([O:64]CC2C=CC=CC=2)[C@@H:62]([CH2:72][OH:73])[O:61][C@@H:32]([O:33][CH2:34][CH:35]([CH2:37][CH2:38][CH2:39][C@H:40]([C@@H:42]2[C@:59]3([CH3:60])[C@H:45]([C@H:46]4[C@H:56]([CH2:57][CH2:58]3)[C@:54]3([CH3:55])[CH:49]([CH2:50][CH2:51][CH2:52][CH2:53]3)[CH2:48][CH2:47]4)[CH2:44][CH2:43]2)[CH3:41])[CH3:36])[C@@H:31]1[O:74]CC1C=CC=CC=1)(=[O:3])[CH3:2].[H][H]>CO.O.C(OCC)(=O)C.[OH-].[OH-].[Pd+2]>[C:1]([NH:4][C@@H:5]1[C@@H:10]([OH:11])[C@H:9]([OH:19])[C@@H:8]([CH2:27][OH:28])[O:7][C@H:6]1[O:29][C@H:30]1[C@@H:63]([OH:64])[C@@H:62]([CH2:72][OH:73])[O:61][C@@H:32]([O:33][CH2:34][CH:35]([CH2:37][CH2:38][CH2:39][C@H:40]([C@@H:42]2[C@:59]3([CH3:60])[C@H:45]([C@H:46]4[C@H:56]([CH2:57][CH2:58]3)[C@:54]3([CH3:55])[CH:49]([CH2:50][CH2:51][CH2:52][CH2:53]3)[CH2:48][CH2:47]4)[CH2:44][CH2:43]2)[CH3:41])[CH3:36])[C@@H:31]1[OH:74])(=[O:3])[CH3:2]

Participants

7

Reactant 2

HCID 86758971HCID 86758971, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86758970HCID 86758970, compoundYield 81.5%

Reagents, catalysts & solvents 4

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Compound 30 (230 mg, 0.209 mmol) was dissolved in a mixture of methanol, water and ethyl acetate (4:1:1, 25 mL), and palladium hydroxide/carbon (230 mg) was added thereto. Inside of the reaction system was replaced with hydrogen gas, and catalytic reduction was performed at room temperature for 20 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=1:1) to obtain Compound 33 (126.1 mg, 81.5%).

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

Sources & evidence

ORD record
ord-3148bb84b43542d1823a11f441d49338
Source dataset
uspto-grants-2003_05
Patent number
US06562954B1

Reaction notes

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