HCID 15157462, compound → HCID 15157463, compound

HRID 2371630Notes

Reaction equation

HRID 2371630 reaction equation
C1(C[O:8][CH2:9][CH:10]([O:20][C:21](=[O:77])[CH2:22][CH2:23][C:24]2([CH2:53][CH2:54][C:55]([O:57][CH:58]([CH2:68][O:69]CC3C=CC=CC=3)[CH2:59][O:60]CC3C=CC=CC=3)=[O:56])[CH2:29][C:28](=[O:30])[C:27]3[CH:31]=[CH:32][C:33]([O:38][CH2:39][CH2:40][CH2:41][O:42][C:43]4[C:52]5[CH2:51][CH2:50][CH2:49][CH2:48][C:47]=5[CH:46]=[CH:45][CH:44]=4)=[C:34]([CH2:35][CH2:36][CH3:37])[C:26]=3[O:25]2)[CH2:11][O:12]CC2C=CC=CC=2)C=CC=CC=1.[H][H]>O1CCCC1.[Pd]>[OH:60][CH2:59][CH:58]([O:57][C:55](=[O:56])[CH2:54][CH2:53][C:24]1([CH2:23][CH2:22][C:21]([O:20][CH:10]([CH2:11][OH:12])[CH2:9][OH:8])=[O:77])[CH2:29][C:28](=[O:30])[C:27]2[CH:31]=[CH:32][C:33]([O:38][CH2:39][CH2:40][CH2:41][O:42][C:43]3[C:52]4[CH2:51][CH2:50][CH2:49][CH2:48][C:47]=4[CH:46]=[CH:45][CH:44]=3)=[C:34]([CH2:35][CH2:36][CH3:37])[C:26]=2[O:25]1)[CH2:68][OH:69]

Participants

5

Reactant 2

HCID 15157462HCID 15157462, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 15157463HCID 15157463, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

The titled product of Example 46 (0.258 g, 0.246 mmol) was dissolved in 25 ml of tetrahydrofuran, and then hydrogenated at room temperature using hydrogen at atmospheric pressure and 10% palladium on carbon (Pd/C) as catalyst. The insolubles were removed by filtration, and the solvent removed under reduced pressure. The residue was chromatographed on silica gel column. Elution with 5% methanol/ethyl acetate afforded 125 mg of the title compound.

Workup

  1. customhydrogenated at room temperature
  2. customThe insolubles were removed by filtration
  3. customthe solvent removed under reduced pressure
  4. customThe residue was chromatographed on silica gel column
  5. washElution with 5% methanol/ethyl acetate

Sources & evidence

ORD record
ord-30c1c175e7f24f789abe514deccb54f9
Source dataset
uspto-grants-1992_03
Patent number
US05093353

Reaction notes

Loading…