HCID 57293204, compound → HCID 131717635, compound

HRID 373266Notes

Reaction equation

HRID 373266 reaction equation
[CH2:1]([CH:3]1[CH:29]=[C:28]([CH3:30])[CH2:27][CH:26]([CH3:31])[CH2:25][CH:24]([O:32][CH3:33])[CH:23]2[O:34][C:19]([OH:38])([CH:20]([CH3:37])[CH2:21][CH:22]2[O:35][CH3:36])[C:18](=[O:39])[C:17](=[O:40])[N:16]2[CH:11]([CH2:12][CH2:13][CH2:14][CH2:15]2)[C:10](=[O:41])[O:9][CH:8]([C:42]([CH3:61])=[CH:43][CH:44]2[CH2:49][CH2:48][CH:47]([O:50][CH2:51][CH:52]=[CH:53][C:54]3[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=3)[CH:46]([OH:60])[CH2:45]2)[CH:7]([CH3:62])[CH2:6][CH2:5][C:4]1=[O:63])[CH3:2].[H][H]>[Rh]>[CH2:1]([CH:3]1[CH:29]=[C:28]([CH3:30])[CH2:27][CH:26]([CH3:31])[CH2:25][CH:24]([O:32][CH3:33])[CH:23]2[O:34][C:19]([OH:38])([CH:20]([CH3:37])[CH2:21][CH:22]2[O:35][CH3:36])[C:18](=[O:39])[C:17](=[O:40])[N:16]2[CH:11]([CH2:12][CH2:13][CH2:14][CH2:15]2)[C:10](=[O:41])[O:9][CH:8]([C:42]([CH3:61])=[CH:43][CH:44]2[CH2:49][CH2:48][CH:47]([O:50][CH2:51][CH2:52][CH2:53][C:54]3[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=3)[CH:46]([OH:60])[CH2:45]2)[CH:7]([CH3:62])[CH2:6][CH2:5][C:4]1=[O:63])[CH3:2]

Participants

4

Reactant 2

HCID 57293204HCID 57293204, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 131717635HCID 131717635, compound

Reagents, catalysts & solvents 1

HCID 23948RhodiumCatalyst

Procedure

To a solution of 17-ethyl-1-hydroxy-12-[2'-(4"-cinnamyloxy-3"-hydroxycyclohexyl)-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 (16 mg in 2 ml ethanol) is added 2 mg of 5% rhodium on carbon catalyst. The reaction flask is fitted with a hydrogen balloon, evacuated and recharged with hydrogen (3 times) and stirred at room temperature. After 30 minutes, the mixture is filtered over diatomaceuis earth, concentrated and purified by preparative TLC on silica gel to give the title compound.

Workup

  1. customevacuated
  2. filtrationthe mixture is filtered over diatomaceuis earth
  3. concentrationconcentrated
  4. custompurified by preparative TLC on silica gel

Sources & evidence

ORD record
ord-7bf55b532653419ea4f51bd86b693f75
Source dataset
uspto-grants-1992_11
Patent number
US05162334

Reaction notes

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