HCID 57314607, compound → HCID 57085116, compound

HRID 248241Notes

Reaction equation

HRID 248241 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][C:47](=[O:50])[CH:46]([O:51][CH3:52])[CH2:45]2)[CH:7]([CH3:54])[CH:6]([O:55][Si](C(C)C)(C(C)C)C(C)C)[CH2:5][C:4]1=[O:66])[CH3:2]>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]([CH3:53])=[CH:43][CH:44]2[CH2:49][CH2:48][C:47](=[O:50])[CH:46]([O:51][CH3:52])[CH2:45]2)[CH:7]([CH3:54])[CH:6]([OH:55])[CH2:5][C:4]1=[O:66])[CH3:2]

Participants

3

Reactant 1

HCID 57314607HCID 57314607, compound

Product 1

HCID 57085116HCID 57085116, compoundYield 82.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of 17-ethyl-1-hydroxy-12-[2'-(3"-methoxy-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 from Example 19 (870 mg) in acetonitrile (20 ml) was added hydrofluroic acid (48%, 1 ml) at room temperature. The reaction progress was monitored by tlc analysis and after 4 hr. the reaction mixture was quenched with sat'd aqueous sodium bicarbonate. The organic layer was separated and the aqueous layer was extracted with ethyl acetate three times. Combined organic layers were washed (sat'd NaHCO3, sat'd NaCl), dried (anhydrous Na2SO4), and filtered. Removal of solvent followed by purification (silica gel column chromatography, 50% ethyl acetate/hexane) gave 600 mg of the title compound.

Workup

  1. customthe reaction mixture was quenched with sat'd aqueous sodium bicarbonate
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with ethyl acetate three times
  4. washCombined organic layers were 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, 50% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-fe5f6cb1041c4986be12603bf66ed8e9
Source dataset
uspto-grants-1993_05
Patent number
US05208228

Reaction notes

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