HCID 77353518, compound → HCID 57234157, compound

HRID 1939093Notes

Reaction equation

HRID 1939093 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-7135592bd3fc4aaeb9b5764c2283f4fb
Source dataset
uspto-grants-1997_12
Patent number
US05693648

Reaction notes

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