HCID 86638445, compound → HCID 24853446, compound

HRID 1009883Notes

Reaction equation

HRID 1009883 reaction equation
C([O:8][C@@H:9]1[C@@H:14]([O:15]CC2C=CC=CC=2)[C@H:13]([O:23]CC2C=CC=CC=2)[C@@H:12]([CH2:31][O:32]CC2C=CC=CC=2)[O:11][C@H:10]1[C:40]1[CH:45]=[C:44]([CH2:46][C:47]2[CH:52]=[CH:51][C:50](/[CH:53]=[CH:54]/[CH2:55][C:56]([NH:58][C:59]([CH2:63][OH:64])([CH3:62])[CH2:60][OH:61])=[O:57])=[CH:49][CH:48]=2)[C:43]([CH3:65])=[CH:42][C:41]=1[O:66]CC1C=CC=CC=1)C1C=CC=CC=1>CO.[Pd].[OH-].[Pd+2].[OH-]>[OH:66][C:41]1[CH:42]=[C:43]([CH3:65])[C:44]([CH2:46][C:47]2[CH:52]=[CH:51][C:50]([CH2:53][CH2:54][CH2:55][C:56]([NH:58][C:59]([CH2:60][OH:61])([CH3:62])[CH2:63][OH:64])=[O:57])=[CH:49][CH:48]=2)=[CH:45][C:40]=1[C@@H:10]1[O:11][C@H:12]([CH2:31][OH:32])[C@@H:13]([OH:23])[C@H:14]([OH:15])[C@H:9]1[OH:8]

Participants

5

Reactant 1

HCID 86638445HCID 86638445, compound

Product 1

HCID 24853446HCID 24853446, compoundYield 65%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent2×

Procedure

To a methanol solution (1 mL) of (1S)-1,5-anhydro-2,3,4,6-tetra-O-benzyl-1-[2-(benzyloxy)-5-[4-[(1E)-4-[[2-hydroxy-1-(hydroxymethyl)-1-methylethyl]amino]-4-oxobut-1-en-1-yl]benzyl]-4-methylphenyl]-D-glucitol (91 mg, 0.0926 mmol) was added 10% palladium-activated carbon (16 mg), and the mixture was stirred overnight under a hydrogen atmosphere at room temperature. The reaction solution was filtered through celite, and evaporated under reduced pressure to obtain a residue. Thus obtained residue was dissolved in methanol (1 mL). And 20% palladium hydroxide (91 mg) was added thereto, and the mixture was stirred under hydrogen atmosphere at room temperature for 2 days. The reaction solution was filtered through celite, and evaporated under reduced pressure to obtain a residue. Thus obtained residue was purified with silica gel column chromatography (chloroform:methanol=5:1) to obtain the title compound (32 mg, 65%) as a colorless powder. NMR data and MS data of the compound are shown in Table 1.

Workup

  1. filtrationThe reaction solution was filtered through celite
  2. customevaporated under reduced pressure
  3. customto obtain a residue
  4. stirringthe mixture was stirred under hydrogen atmosphere at room temperature for 2 days
  5. filtrationThe reaction solution was filtered through celite
  6. customevaporated under reduced pressure
  7. customto obtain a residue
  8. customThus obtained residue was purified with silica gel column chromatography (chloroform:methanol=5:1)

Sources & evidence

ORD record
ord-0320aaea0f61426787c353533c47dabd
Source dataset
uspto-grants-2011_07
Patent number
US07973012B2

Reaction notes

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