HCID 56635383, compound → HCID 15459991, compound

HRID 2288103Notes

Reaction equation

HRID 2288103 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:51]([O:52][Si](C(C)(C)C)(C)C)[CH:41]6[CH:42]([O:43][CH2:44][C:45]7[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=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:60]([CH3:62])[CH3:61])=[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:60]([CH3:62])[CH3:61])=[CH:19]6)[CH:27]4[CH:23]([CH:24]([CH3:32])[CH2:25][CH2:26]4)[CH2:22]5)([CH:51]([OH:52])[CH:41]1[O:40]3)[O:36]2)[C:45]1[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=1

Participants

4

Reactant 1

HCID 56635383HCID 56635383, compound

Product 1

HCID 15459991HCID 15459991, compoundYield 98.9%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

15 mg of compound (75) 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×30 cm) and eluted with chloroform-methanol (20:1). The fraction containing the desired product was concentrated to dryness to give 10.0 mg of compound (76).

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 (20:1)
  5. additionThe fraction containing the desired product
  6. concentrationwas concentrated to dryness

Sources & evidence

ORD record
ord-62257db13bd04281800ec05cc5da443f
Source dataset
uspto-grants-2000_07
Patent number
US06087390

Reaction notes

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