HCID 77353518, compound → HCID 57234157, compound

HRID 865586Notes

Reaction equation

HRID 865586 reaction equation
[H][H].[CH2:3]([CH:5]1[CH:31]=[C:30]([CH3:32])[CH2:29][CH:28]([CH3:33])[CH2:27][CH:26]([O:34][CH3:35])[CH:25]2[O:36][C:21]([OH:40])([CH:22]([CH3:39])[CH2:23][CH:24]2[O:37][CH3:38])[C:20](=[O:41])[C:19](=[O:42])[N:18]2[CH:13]([CH2:14][CH2:15][CH2:16][CH2:17]2)[C:12](=[O:43])[O:11][CH:10]([C:44]([CH3:60])=[CH:45][CH:46]2[CH2:51][CH2:50][CH:49]([O:52][CH2:53][CH:54]=[CH2:55])[CH:48]([O:56][CH2:57][CH:58]=[CH2:59])[CH2:47]2)[CH:9]([CH3:61])[CH2:8][CH2:7][C:6]1=[O:62])[CH3:4]>[Rh]>[CH2:3]([CH:5]1[CH:31]=[C:30]([CH3:32])[CH2:29][CH:28]([CH3:33])[CH2:27][CH:26]([O:34][CH3:35])[CH:25]2[O:36][C:21]([OH:40])([CH:22]([CH3:39])[CH2:23][CH:24]2[O:37][CH3:38])[C:20](=[O:41])[C:19](=[O:42])[N:18]2[CH:13]([CH2:14][CH2:15][CH2:16][CH2:17]2)[C:12](=[O:43])[O:11][CH:10]([C:44]([CH3:60])=[CH:45][CH:46]2[CH2:51][CH2:50][CH:49]([O:52][CH2:53][CH2:54][CH3:55])[CH:48]([O:56][CH2:57][CH2:58][CH3:59])[CH2:47]2)[CH:9]([CH3:61])[CH2:8][CH2:7][C:6]1=[O:62])[CH3:4]

Participants

4

Reactant 2

HCID 77353518HCID 77353518, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 57234157HCID 57234157, compoundYield 65.9%

Reagents, catalysts & solvents 1

HCID 23948RhodiumCatalyst

Procedure

To a solution of 17-ethyl-1-hydroxy-12-[2'-(3",4"-diallyloxycyclohexyl)-1'-methylvinyl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9 ]octacos-18-ene-2,3,10,16-tetraone (6.8 mg in 600 μl ethyl acetate) was added 4 mg of 5% rhodium on carbon catalyst. The reaction flask was fitted with a hydrogen balloon, evacuated and recharged with hydrogen (3 times) and stirred at room temperature. After 25 minutes, the mixture was filtered over Celite, concentrated and purified by flash chromatography on silica gel (ethyl acetate: hexane (1:3)+1% methanol) to give the title compound (4.5 mg).

Workup

  1. customevacuated
  2. filtrationthe mixture was filtered over Celite
  3. concentrationconcentrated
  4. custompurified by flash chromatography on silica gel (ethyl acetate: hexane (1:3)+1% methanol)

Sources & evidence

ORD record
ord-9842ce5b1db04756af49d7c3bdcf57b7
Source dataset
uspto-grants-1996_10
Patent number
US05565560

Reaction notes

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