17-Ethyl-1,14,20-trihydroxy-12-[2'-(4"-hydroxy-3"-methoxycyclohexyl)-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 → 17-Ethyl-1,20-dihydroxy-12-[2'-(4"-hydroxy-3"-methoxycyclohexyl)-1'-methylvinyl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9]octacos-14,18-diene-2,3,10,16-tetraone

HRID 1742912

Reaction equation

HRID 1742912 reaction equation
[CH2:1]([CH:3]1[CH:29]=[C:28]([CH3:30])[CH:27]([OH:31])[CH:26]([CH3:32])[CH2:25][CH:24]([O:33][CH3:34])[CH:23]2[O:35][C:19]([OH:39])([CH:20]([CH3:38])[CH2:21][CH:22]2[O:36][CH3:37])[C:18](=[O:40])[C:17](=[O:41])[N:16]2[CH:11]([CH2:12][CH2:13][CH2:14][CH2:15]2)[C:10](=[O:42])[O:9][CH:8]([C:43]([CH3:54])=[CH:44][CH:45]2[CH2:50][CH2:49][CH:48]([OH:51])[CH:47]([O:52][CH3:53])[CH2:46]2)[CH:7]([CH3:55])[CH:6](O)[CH2:5][C:4]1=[O:57])[CH3:2].C1(C)C=CC(S(O)(=O)=O)=CC=1.C([O-])(O)=O.[Na+]>>[CH2:1]([CH:3]1[CH:29]=[C:28]([CH3:30])[CH:27]([OH:31])[CH:26]([CH3:32])[CH2:25][CH:24]([O:33][CH3:34])[CH:23]2[O:35][C:19]([OH:39])([CH:20]([CH3:38])[CH2:21][CH:22]2[O:36][CH3:37])[C:18](=[O:40])[C:17](=[O:41])[N:16]2[CH:11]([CH2:12][CH2:13][CH2:14][CH2:15]2)[C:10](=[O:42])[O:9][CH:8]([C:43]([CH3:54])=[CH:44][CH:45]2[CH2:50][CH2:49][CH:48]([OH:51])[CH:47]([O:52][CH3:53])[CH2:46]2)[CH:7]([CH3:55])[CH:6]=[CH:5][C:4]1=[O:57])[CH3:2]

Participants

4

Reactant 3

HCID 385017-Ethyl-1,14,20-trihydroxy-12-[2'-(4"-hydroxy-3"-methoxycyclohexyl)-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-tetraoneHCID 6101p-Toluenesulfonic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 5698798517-Ethyl-1,20-dihydroxy-12-[2'-(4"-hydroxy-3"-methoxycyclohexyl)-1'-methylvinyl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9]octacos-14,18-diene-2,3,10,16-tetraone

Conditions

Temperature
60 °C

Procedure

To a stirred solution of 17-ethyl-1,14,20-trihydroxy-12-[2'-(4"-hydroxy-3"-methoxycyclohexyl)-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 (in benzene) is added p-toluenesulfonic acid and the mixture warmed to 60° C. in an oil bath. The reaction mixture is cooled to room temperature, neutralized by the addition of a saturated aqueous NaHCO3 solution and extracted with ethyl acetate (3 times). The combined organics are washed with saturated NaCl solution, dried over Na2SO4 and purified by flash chromatography on silica gel (20% hexanes in ethyl acetate and 1% MeOH) to yield the title compound.

Workup

  1. temperatureThe reaction mixture is cooled to room temperature
  2. extractionextracted with ethyl acetate (3 times)
  3. washThe combined organics are washed with saturated NaCl solution
  4. dry with materialdried over Na2SO4
  5. custompurified by flash chromatography on silica gel (20% hexanes in ethyl acetate and 1% MeOH)

Sources & evidence

ORD record
ord-496d499b03684325846aa36ee2e4b566
Source dataset
uspto-grants-1994_08
Patent number
US05342935

Linked notes

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