HCID 56637837, compound → HCID 18703944, compound

HRID 2288082Notes

Reaction equation

HRID 2288082 reaction equation
C1(C([O:14][C:15]([C:17]23[C:28]4([CH:30]=[O:31])[CH2:29][CH:20]([C:21]2([CH2:33][O:34][C:35]25[CH:47]([OH:48])[CH:41]6[CH:42]([O:43][CH:44]([CH3:46])[CH3:45])[CH:37]([CH:38]([O:40]6)[O:39]2)[O:36]5)[CH2:22][CH:23]2[CH:27]4[CH2:26][CH2:25][CH:24]2[CH3:32])[CH:19]=[C:18]3[CH:49]([CH3:51])[CH3:50])=[O:16])C2C=CC=CC=2)C=CC=CC=1>C(OCC)(=O)C.[C].[Pd]>[CH:44]([O:43][CH:42]1[CH:37]2[CH:38]3[O:39][C:35]([O:34][CH2:33][C:21]45[CH:20]6[CH2:29][C:28]([CH:30]=[O:31])([C:17]4([C:15]([OH:16])=[O:14])[C:18]([CH:49]([CH3:51])[CH3:50])=[CH:19]6)[CH:27]4[CH:23]([CH:24]([CH3:32])[CH2:25][CH2:26]4)[CH2:22]5)([CH:47]([OH:48])[CH:41]1[O:40]3)[O:36]2)([CH3:45])[CH3:46]

Participants

4

Reactant 1

HCID 56637837HCID 56637837, compound

Product 1

HCID 18703944HCID 18703944, compoundYield 99.1%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

9 mg of compound (34) was dissolved in 2 ml of ethyl acetate and allowed to react in the presence of a catalytic amount of 10% palladium-carbon under stirring under a hydrogen atmosphere at room temperature for 2 hours. The reaction solution was filtered, and the filtrate was concentrated in vacuo. The reaction product was charged onto a silica gel column (Kieselgel 60, Merck, 1.0φ×30 cm) and eluted with chloroform-methanol (30:1). The fraction containing the desired product was concentrated to dryness to give 6.8 mg of compound (35).

Workup

  1. filtrationThe reaction solution was filtered
  2. concentrationthe filtrate was concentrated in vacuo
  3. additionThe reaction product was charged onto a silica gel column (Kieselgel 60, Merck, 1.0φ×30 cm)
  4. washeluted with chloroform-methanol (30:1)
  5. additionThe fraction containing the desired product
  6. concentrationwas concentrated to dryness

Sources & evidence

ORD record
ord-c6dee0f3ccd841889ce93ba1f08d3fd1
Source dataset
uspto-grants-2000_07
Patent number
US06087390

Reaction notes

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