HCID 56626734, compound → HCID 56618848, compound

HRID 2288099Notes

Reaction equation

HRID 2288099 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][C:47]#[N: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]>[C:47]([CH2:46][CH2:45][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)#[N:48]

Participants

4

Reactant 1

HCID 56626734HCID 56626734, compound

Product 1

HCID 56618848HCID 56618848, compoundYield 27.3%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

20 mg of compound (64) was dissolved in 3 ml of ethyl acetate and stirred together with a catalytic amount of 10% palladium-carbon under a hydrogen atmosphere at room temperature for 1.5 hours. The reaction solution was filtered and concentrated in vacuo. The reaction product was dissolved in 10 ml of methanol and washed with 10 ml of n-hexane four times, and the lower layer was concentrated in vacuo to give 4.2 mg of compound (65) as a colorless solid.

Workup

  1. filtrationThe reaction solution was filtered
  2. concentrationconcentrated in vacuo
  3. dissolutionThe reaction product was dissolved in 10 ml of methanol
  4. washwashed with 10 ml of n-hexane four times
  5. concentrationthe lower layer was concentrated in vacuo

Sources & evidence

ORD record
ord-4ddef931e1144709b6926d3247f628a0
Source dataset
uspto-grants-2000_07
Patent number
US06087390

Reaction notes

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