HCID 56634000, compound → HCID 56620726, compound

HRID 2288102Notes

Reaction equation

HRID 2288102 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:55]([OH:56])[CH:41]6[CH:42]([O:43][CH2:44][CH2:45][CH2:46][O:47]CC7C=CC=CC=7)[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:57]([CH3:59])[CH3:58])=[O:16])C2C=CC=CC=2)C=CC=CC=1>C(OCC)(=O)C.[C].[Pd]>[OH: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:57]([CH3:58])[CH3:59])=[CH:19]6)[CH:27]4[CH:23]([CH:24]([CH3:32])[CH2:25][CH2:26]4)[CH2:22]5)([CH:55]([OH:56])[CH:41]1[O:40]3)[O:36]2

Participants

4

Reactant 1

HCID 56634000HCID 56634000, compound

Product 1

HCID 56620726HCID 56620726, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

38.3 mg of compound (73) was dissolved in 0.9 ml of ethyl acetate and stirred together with a catalytic amount of 10% palladium-carbon under a hydrogen atmosphere at room temperature for 2.5 hours. The reaction solution was filtered and concentrated in vacuo. The reaction product was dissolved in 10 ml of methanol and washed with 15 ml of n-hexane four times, and the lower layer was concentrated in vacuo to give 23.5 mg of compound (74) 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 15 ml of n-hexane four times
  5. concentrationthe lower layer was concentrated in vacuo

Sources & evidence

ORD record
ord-9ca86947b1bc41dda5630d658cad5a10
Source dataset
uspto-grants-2000_07
Patent number
US06087390

Reaction notes

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