HCID 86753845, compound → HCID 86753844, compound

HRID 1417635Notes

Reaction equation

HRID 1417635 reaction equation
C([O:8][C:9]1[C:10]2[CH2:23][C@:22]3([CH3:36])[C@@H:24]([CH3:35])[CH2:25][CH2:26][C@H:27]4[C:28]([CH3:34])([CH3:33])[C@@H:29]([OH:32])[CH2:30][CH2:31][C@@:21]34[O:20][C:11]=2[C:12]2[C@H:13]([CH3:19])[NH:14][C:15](=[O:18])[C:16]=2[CH:17]=1)C1C=CC=CC=1>CO.[C].[Pd]>[OH:8][C:9]1[C:10]2[CH2:23][C@:22]3([CH3:36])[C@@H:24]([CH3:35])[CH2:25][CH2:26][C@H:27]4[C:28]([CH3:34])([CH3:33])[C@@H:29]([OH:32])[CH2:30][CH2:31][C@@:21]34[O:20][C:11]=2[C:12]2[C@H:13]([CH3:19])[NH:14][C:15](=[O:18])[C:16]=2[CH:17]=1

Participants

4

Reactant 1

HCID 86753845HCID 86753845, compound

Product 1

HCID 86753844HCID 86753844, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

To Compound (66a) (28 mg, 0.06 mmol) dissolved in 15 ml of methanol containing 10% water was added 20 mg of 10% palladium-carbon, followed by catalytic reduction for 2.5 hours. After the palladium-carbon was removed by filtration, the filtrate was concentrated under reduced pressure. The residue was purified by a silica gel column chromatography (silica gel 5 g; ethyl acetate: methanol=19:1) and by crystallization from diethyl ether-n-hexane to give 17 mg (74%) of Compound (67a). Melting point: 280°-285° C. (decomp.) Elemental analysis for C24H33NO4.5/2 H2O Calcd.: C, 64.84%; H, 8.62%; N, 3.15% Found: C, 64.53%; H, 8.94%; N, 3.28%

Workup

  1. customAfter the palladium-carbon was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by a silica gel column chromatography (silica gel 5 g; ethyl acetate: methanol=19:1) and by crystallization from diethyl ether-n-hexane

Sources & evidence

ORD record
ord-3e4fe4e2ed8e4024b832f9a33bf8dff9
Source dataset
uspto-grants-1999_03
Patent number
US05876984

Reaction notes

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