p-Toluenesulfonic acid → HCID 57205229, compound

HRID 2226797Notes

Reaction equation

HRID 2226797 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]([CH3:73])=[CH:43][CH:44]2[CH2:49][CH2:48][CH:47]([O:50][C:51]3[CH:59]=[C:58]4[C:54]([CH:55]=[CH:56][N:57]4[CH2:60][CH2:61][CH2:62][O:63][Si](C(C)(C)C)(C)C)=[CH:53][CH:52]=3)[CH:46]([O:71][CH3:72])[CH2:45]2)[CH:7]([CH3:74])[CH:6]([OH:75])[CH2:5][C:4]1=[O:76])[CH3:2].C1(C)C=CC(S(O)(=O)=O)=CC=1>C(Cl)Cl.CO>[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]([CH3:73])=[CH:43][CH:44]2[CH2:49][CH2:48][CH:47]([O:50][C:51]3[CH:59]=[C:58]4[C:54]([CH:55]=[CH:56][N:57]4[CH2:60][CH2:61][CH2:62][OH:63])=[CH:53][CH:52]=3)[CH:46]([O:71][CH3:72])[CH2:45]2)[CH:7]([CH3:74])[CH:6]([OH:75])[CH2:5][C:4]1=[O:76])[CH3:2]

Participants

5

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 57241222HCID 57241222, compound

Product 1

HCID 57205229HCID 57205229, compoundYield 66.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 17-Ethyl-1,14-dihydroxy -12-[2'-(4"-(1-(3-t-butyldimethylsilyloxypropyl)indol -6-yl)oxy-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-tetra -one (318 mg) in CH2Cl2 (5 mL) at rt was added a solution of p-toluene sulfonic acid (25 mg) in CH3OH (5 mL). The reaction mixture was stirred for 3 hours quenched with saturated NaHCO3, then extracted with CH2Cl2. The extracts were combined, dried over Na2SO4, filtered and concentrated in vacuo. The product was purified by preparative TLC on silica gel (2:1,hexane/acetone) to give 190 mg of the title compound.

Workup

  1. customquenched with saturated NaHCO3
  2. extractionextracted with CH2Cl2
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe product was purified by preparative TLC on silica gel (2:1,hexane/acetone)

Sources & evidence

ORD record
ord-bf15a2c21e634cad82f537208c06b4ae
Source dataset
uspto-grants-1994_09
Patent number
US05349061

Reaction notes

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