p-Toluenesulfonic acid → HCID 57163898, compound

HRID 1492946Notes

Reaction equation

HRID 1492946 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]([CH3:55])=[CH:44][CH:45]2[CH2:50][CH2:49][CH:48]([O:51][CH3:52])[CH:47]([O:53][CH3:54])[CH2:46]2)[CH:8]([CH3:56])[CH:7](O)[CH2:6][C:5]1=[O:58])[CH:2]=[CH2:3].CC1C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[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]([CH3:55])=[CH:44][CH:45]2[CH2:50][CH2:49][CH:48]([O:51][CH3:52])[CH:47]([O:53][CH3:54])[CH2:46]2)[CH:8]([CH3:56])[CH:7]=[CH:6][C:5]1=[O:58])[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 67799152HCID 67799152, compound

Product 1

HCID 57163898HCID 57163898, compoundYield 81.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A stirred solution of 17-Allyl-1,14-dihydroxy-12-[2-(3,4-dimethoxycyclohexyl)-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 (10 mg, prepared by methylation of macrolide FR 900506), in toluene (5 ml) containing a trace of tosic acid was heated on a steam bath for 5 minutes. Removal of solvent in vacuo and chromatography on silica eluting with ethyl acetate gave the title compound as an oil (8 mg).

Workup

  1. temperaturewas heated on a steam bath for 5 minutes
  2. customRemoval of solvent in vacuo and chromatography on silica eluting with ethyl acetate

Sources & evidence

ORD record
ord-3e9f2628bf73465fa354d993d1740b0e
Source dataset
uspto-grants-1994_12
Patent number
US05376663

Reaction notes

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