Hydrofluoric Acid → HCID 57196378, compound

HRID 373283Notes

Reaction equation

HRID 373283 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]([CH3:55])=[CH:43][CH:44]2[CH2:49][CH2:48][C:47](=[O:50])[CH:46]([O:51][CH2:52][CH:53]=[CH2:54])[CH2:45]2)[CH:7]([CH3:56])[CH:6]([O:57][Si](C(C)C)(C(C)C)C(C)C)[CH2:5][C:4]1=[O:68])[CH3:2].F>C(#N)C>[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]([CH3:55])=[CH:43][CH:44]2[CH2:49][CH2:48][C:47](=[O:50])[CH:46]([O:51][CH2:52][CH:53]=[CH2:54])[CH2:45]2)[CH:7]([CH3:56])[CH:6]([OH:57])[CH2:5][C:4]1=[O:68])[CH3:2]

Participants

4

Reactant 2

HCID 14917Hydrofluoric AcidHCID 57251512HCID 57251512, compound

Product 1

HCID 57196378HCID 57196378, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of 17-ethyl-1-hydroxy-12-[2'-(3"-allyloxy-4"-oxocyclohexyl)-1'-methylvinyl]-14-triisopropylsilyloxy-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 acetonitrile was added hydrofluoric acid at room temperature. The reaction progress is monitored by tlc analysis. The reaction mixture is quenched with sat'd aqueous sodium bicarbonate. The organic layer is separated and the aqueous layer is extracted with ethyl acetate three times. Combined organic layers are washed (sat'd NaHCO3, sat'd NaCl), dried (anhydrous Na2SO4), and filtered. Removal of solvent followed by purification (silica gel column chromatography), gives the title compound.

Workup

  1. customThe reaction mixture is quenched with sat'd aqueous sodium bicarbonate
  2. customThe organic layer is separated
  3. extractionthe aqueous layer is extracted with ethyl acetate three times
  4. washCombined organic layers are washed (sat'd NaHCO3, sat'd NaCl)
  5. dry with materialdried (anhydrous Na2SO4)
  6. filtrationfiltered
  7. customRemoval of solvent
  8. customfollowed by purification (silica gel column chromatography)

Sources & evidence

ORD record
ord-b374558475cd49ee963c3a18c5564942
Source dataset
uspto-grants-1992_11
Patent number
US05162334

Reaction notes

Loading…