HCID 15459994, compound → HCID 15459995, compound

HRID 2288087Notes

Reaction equation

HRID 2288087 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:49]([OH:50])[CH:41]6[CH:42]([O:43][CH2:44][CH2:45][CH2:46][CH2:47][CH3:48])[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:51]([CH3:53])[CH3:52])=[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:51]([CH3:52])[CH3:53])=[CH:19]6)[CH:27]4[CH:23]([CH:24]([CH3:32])[CH2:25][CH2:26]4)[CH2:22]5)([CH:49]([OH:50])[CH:41]1[O:40]3)[O:36]2)[CH2:45][CH2:46][CH2:47][CH3:48]

Participants

4

Reactant 1

HCID 15459994HCID 15459994, compound

Product 1

HCID 15459995HCID 15459995, compoundYield 99.4%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

15 mg of compound (40) 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 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×30 cm) and eluted with chloroform-methanol (40:1). The fraction containing the desired product was concentrated to dryness to give 11.5 mg of compound (41).

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 (40:1)
  5. additionThe fraction containing the desired product
  6. concentrationwas concentrated to dryness

Sources & evidence

ORD record
ord-a968306c27d04a19bb5925c7f13649ff
Source dataset
uspto-grants-2000_07
Patent number
US06087390

Reaction notes

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