HCID 57192441, compound → HCID 18703963, compound

HRID 2288100Notes

Reaction equation

HRID 2288100 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:50]([OH:51])[CH:41]6[CH:42]([O:43][CH2:44][C:45]([O:47][CH2:48][CH3:49])=[O:46])[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:52]([CH3:54])[CH3:53])=[O:16])C2C=CC=CC=2)C=CC=CC=1>C(OCC)(=O)C.[C].[Pd]>[CH2:48]([O:47][C: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:52]([CH3:54])[CH3:53])=[CH:19]6)[CH:27]4[CH:23]([CH:24]([CH3:32])[CH2:25][CH2:26]4)[CH2:22]5)([CH:50]([OH:51])[CH:41]1[O:40]3)[O:36]2)=[O:46])[CH3:49]

Participants

4

Reactant 1

HCID 57192441HCID 57192441, compound

Product 1

HCID 18703963HCID 18703963, compoundYield 39.1%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

22.4 mg of compound (67) 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 5 ml of methanol and washed with 5 ml of n-hexane twice, and the lower layer was concentrated in vacuo to give 6.8 mg of compound (68) as a colorless solid.

Workup

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

Sources & evidence

ORD record
ord-378296ceefbb444b803ef237e0c0ca99
Source dataset
uspto-grants-2000_07
Patent number
US06087390

Reaction notes

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