17-Ethyl-1,14-dihydroxy-12-[1-(4-hydroxy-3-methoxycyclohexyl)prop-1-en-2-yl]-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-tetrone → 17-Ethyl-1-hydroxy-12-[2-(4-hydroxy-3-methoxycyclo hexyl)-1-methylvinyl]-23,25-dimethoxy-13,19,21,27-tetra methyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9]octacos-14,18-diene-2.3,10,16-tetraone

HRID 487828

Reaction equation

HRID 487828 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]([CH3:53])=[CH:43][CH:44]2[CH2:49][CH2:48][CH:47]([OH:50])[CH:46]([O:51][CH3:52])[CH2:45]2)[CH:7]([CH3:54])[CH:6](O)[CH2:5][C:4]1=[O:56])[CH3:2].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[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]([CH3:53])=[CH:43][CH:44]2[CH2:49][CH2:48][CH:47]([OH:50])[CH:46]([O:51][CH3:52])[CH2:45]2)[CH:7]([CH3:54])[CH:6]=[CH:5][C:4]1=[O:56])[CH3:2]

Participants

4

Reactant 2

HCID 224117-Ethyl-1,14-dihydroxy-12-[1-(4-hydroxy-3-methoxycyclohexyl)prop-1-en-2-yl]-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-tetroneHCID 6101p-Toluenesulfonic acid

Product 1

HCID 5728575117-Ethyl-1-hydroxy-12-[2-(4-hydroxy-3-methoxycyclo hexyl)-1-methylvinyl]-23,25-dimethoxy-13,19,21,27-tetra methyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9]octacos-14,18-diene-2.3,10,16-tetraoneYield 81.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

17-Ethyl-1,14-dihydroxy-12-[2-(4-hydroxy-3-methoxycyclo hexyl)-1-methylvinyl)-23,25-dimethoxy-13,19,21,27-tetra methyl-11,28-dioxa-4-azatricyclo(22.3.1.04,9 ]octacos-18-ene-2,3,10,16-tetraone (FR-900520) (100 mg) and p-toluenesulphonic acid (2 mg) were dissolved in dry toluene (20 ml) and were heated for 2 hours at 100° C. under an atmosphere of nitrogen. Removal of solvent in vacuo and chromatography on silica eluting with hexane/acetone [2:1] gave the sub-title compound as a foam (80 mg).

Workup

  1. customRemoval of solvent in vacuo and chromatography on silica eluting with hexane/acetone [2:1]

Sources & evidence

ORD record
ord-9decd6b5e90d40f38a94ea670b681482
Source dataset
uspto-grants-1994_03
Patent number
US05296489

Linked notes

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