HCID 15459992, compound → HCID 15459993, compound

HRID 2288085Notes

Reaction equation

HRID 2288085 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:48]([OH:49])[CH:41]6[CH:42]([O:43][CH2:44][CH2:45][CH2:46][CH3:47])[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:50]([CH3:52])[CH3:51])=[O:16])C2C=CC=CC=2)C=CC=CC=1>C(OCC)(=O)C.[C].[Pd]>[CH2:44]([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:50]([CH3:51])[CH3:52])=[CH:19]6)[CH:27]4[CH:23]([CH:24]([CH3:32])[CH2:25][CH2:26]4)[CH2:22]5)([CH:48]([OH:49])[CH:41]1[O:40]3)[O:36]2)[CH2:45][CH2:46][CH3:47]

Participants

4

Reactant 1

HCID 15459992HCID 15459992, compound

Product 1

HCID 15459993HCID 15459993, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

20.5 mg of compound (37) was dissolved in 1 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 1 hour. 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×22 cm) and eluted with n-hexane-ethyl acetate (1:1) to give 8.8 mg of compound (38) as a colorless oily substance.

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×22 cm)
  4. washeluted with n-hexane-ethyl acetate (1:1)

Sources & evidence

ORD record
ord-1147897ae2804b4ba848ad611f1c66da
Source dataset
uspto-grants-2000_07
Patent number
US06087390

Reaction notes

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