p-Toluenesulfonic acid → HCID 57167750, compound

HRID 1492952Notes

Reaction equation

HRID 1492952 reaction equation
[CH2:1]([CH:4]1[CH:30]=[C:29]([CH3:31])[CH2:28][CH:27]([CH3:32])[CH2:26][CH:25]([O:33][CH3:34])[CH:24]2[O:35][C:20]([OH:39])([CH:21]([CH3:38])[CH2:22][CH:23]2[O:36][CH3:37])[C:19](=[O:40])[C:18](=[O:41])[N:17]2[CH:12]([CH2:13][CH2:14][CH2:15][CH2:16]2)[C:11](=[O:42])[O:10][CH:9]([C:43]([CH3:53])=[CH:44][CH:45]2[CH2:50][CH2:49][CH:48]([OH:51])[CH:47]([OH:52])[CH2:46]2)[CH:8]([CH3:54])[CH:7](O)[CH2:6][C:5]1=[O:56])[CH:2]=[CH2:3].C1(C)C=CC(S(O)(=O)=O)=CC=1.[H][H]>C1(C)C=CC=CC=1.CO.[Pd]>[CH2:1]([CH:4]1[CH:30]=[C:29]([CH3:31])[CH2:28][CH:27]([CH3:32])[CH2:26][CH:25]([O:33][CH3:34])[CH:24]2[O:35][C:20]([OH:39])([CH:21]([CH3:38])[CH2:22][CH:23]2[O:36][CH3:37])[C:19](=[O:40])[C:18](=[O:41])[N:17]2[CH:12]([CH2:13][CH2:14][CH2:15][CH2:16]2)[C:11](=[O:42])[O:10][CH:9]([C:43]([CH3:53])=[CH:44][CH:45]2[CH2:50][CH2:49][CH:48]([OH:51])[CH:47]([OH:52])[CH2:46]2)[CH:8]([CH3:54])[CH2:7][CH2:6][C:5]1=[O:56])[CH2:2][CH3:3]

Participants

7

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 195811HCID 195811, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 57167750HCID 57167750, compoundYield 40.7%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

To a solution of 17-Allyl-1,14-dihydroxy-12-[2-(3,4-dihydroxycyclohexyl)-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 (100 mg) in toluene (20 ml) was added p-toluenesulphonic acid (5 mg) and the resulting solution was warmed for 90 minutes on a steam bath. Evaporation of volatiles in vacuo and chromatography of the residue on silica eluting with ethyl acetate gave an oil which was dissolved in methanol (5 ml). To this was then added 10% palladium-on-carbon (20 mg) and the mixture was stirred in an atmosphere of hydrogen for 1 hour at room temperature. The reaction mixture was then filtered through celite, concentrated in vacuo and purified by chromatography on silica eluting with ethyl acetate to give the title compound as an oil (40 mg).

Workup

  1. temperaturethe resulting solution was warmed for 90 minutes on a steam bath
  2. customEvaporation of volatiles in vacuo and chromatography of the residue on silica eluting with ethyl acetate
  3. customgave an oil which
  4. filtrationThe reaction mixture was then filtered through celite
  5. concentrationconcentrated in vacuo
  6. custompurified by chromatography on silica eluting with ethyl acetate

Sources & evidence

ORD record
ord-c57f2455b43a422290261b7db1c62590
Source dataset
uspto-grants-1994_12
Patent number
US05376663

Reaction notes

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