p-Toluenesulfonic acid → HCID 131720349, compound

HRID 1939101Notes

Reaction equation

HRID 1939101 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]([CH3:69])=[CH:43][CH:44]2[CH2:49][CH2:48][CH:47]([O:50][CH2:51][C:52]3[CH:57]=[CH:56][C:55]([CH2:58][O:59][Si](C(C)(C)C)(C)C)=[CH:54][CH:53]=3)[CH:46]([O:67][CH3:68])[CH2:45]2)[CH:7]([CH3:70])[CH:6]([O:71][Si](C(C)(C)C)(C)C)[CH2:5][C:4]1=[O:79])[CH3:2].C1(C)C=CC(S(O)(=O)=[O:87])=CC=1>C(Cl)Cl>[CH2:1]([CH:3]1[CH:29]=[C:28]([CH3:27])[CH2:30][CH:20]([CH3:37])[CH2:21][CH:22]([O:35][CH3:36])[CH:23]2[O:34][C:19]([OH:38])([CH:26]([CH3:31])[CH2:25][CH:24]2[O:32][CH3:33])[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]([CH3:69])=[CH:43][CH:44]2[CH2:49][CH2:48][CH:47]([O:50][CH2:51][C:52]3[CH:53]=[CH:54][C:55]([C:58]([OH:59])=[O:87])=[CH:56][CH:57]=3)[CH:46]([O:67][CH3:68])[CH2:45]2)[CH:7]([CH3:70])[CH:6]([OH:71])[CH2:5][C:4]1=[O:79])[CH3:2]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 131720350HCID 131720350, compound

Product 1

HCID 131720349HCID 131720349, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 17-ethyl-1-hydroxy-14-(tert-butyldimethylsiloxy)-12-[2'-(4"-(p-(tert-butyldimethylsiloxymethyl)-benzyloxy)-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 (420 mg) in methylene chloride (10 mL) was added a methanolic solution of p-toluenesulfonic acid (10 mL of a 10% solution w/v) and the mixture stirred at room temperature. After 5 minutes, the reaction was cooled to 0° C. and quenched by the careful addition of saturated sodium bicarbonate solution. The mixture was extracted with ethyl acetate and the organic portion washed with brine, dried over magnesium sulfate, and the concentrate purified by flash chromatography on silica gel (ethyl acetate:hexane (1:1+1% methanol) to give the title compound (316 mg).

Workup

  1. temperaturethe reaction was cooled to 0° C.
  2. customquenched by the careful addition of saturated sodium bicarbonate solution
  3. extractionThe mixture was extracted with ethyl acetate
  4. washthe organic portion washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customthe concentrate purified by flash chromatography on silica gel (ethyl acetate:hexane (1:1+1% methanol)

Sources & evidence

ORD record
ord-d35bbcd5fbb74277b9f77c50cfdc5b0e
Source dataset
uspto-grants-1997_12
Patent number
US05693648

Reaction notes

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