HCID 56622945, compound → HCID 18703949, compound

HRID 2288079Notes

Reaction equation

HRID 2288079 reaction equation
CC([O:10][C:11]([C:13]12[C:24]3([CH:26]=[O:27])[CH2:25][CH:16]([C:17]1([CH2:29][O:30][C:31]14[CH:43]([OH:44])[CH:37]5[CH:38]([O:39][CH2:40][CH2:41][CH3:42])[CH:33]([CH:34]([O:36]5)[O:35]1)[O:32]4)[CH2:18][CH:19]1[CH:23]3[CH2:22][CH2:21][CH:20]1[CH3:28])[CH:15]=[C:14]2[CH:45]([CH3:47])[CH3:46])=[O:12])(C)C1C=CC=CC=1>C(OCC)(=O)C.[C].[Pd]>[CH2:40]([O:39][CH:38]1[CH:33]2[CH:34]3[O:35][C:31]([O:30][CH2:29][C:17]45[CH:16]6[CH2:25][C:24]([CH:26]=[O:27])([C:13]4([C:11]([OH:12])=[O:10])[C:14]([CH:45]([CH3:47])[CH3:46])=[CH:15]6)[CH:23]4[CH:19]([CH:20]([CH3:28])[CH2:21][CH2:22]4)[CH2:18]5)([CH:43]([OH:44])[CH:37]1[O:36]3)[O:32]2)[CH2:41][CH3:42]

Participants

4

Reactant 1

HCID 56622945HCID 56622945, compound

Product 1

HCID 18703949HCID 18703949, compoundYield 84.6%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

13 mg of compound (31) 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 (20:1). The fraction containing the desired product was concentrated to dryness to give 9.0 mg of compound (32).

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-c038666bbffe459d82e4d1957872e92c
Source dataset
uspto-grants-2000_07
Patent number
US06087390

Reaction notes

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