Pyridine, hydrofluoride (1:1) → HCID 57305705, compound

HRID 2082621Notes

Reaction equation

HRID 2082621 reaction equation
[CH2:1]([CH:3]1[CH:29]=[C:28]([CH3:30])[CH:27]([F:31])[CH:26]([CH3:32])[CH2:25][CH:24]([O:33][CH3:34])[CH:23]2[O:35][C:19]([OH:39])([CH:20]([CH3:38])[CH2:21][CH:22]2[O:36][CH3:37])[C:18](=[O:40])[C:17](=[O:41])[N:16]2[CH:11]([CH2:12][CH2:13][CH2:14][CH2:15]2)[C:10](=[O:42])[O:9][CH:8]([C:43]([CH3:54])=[CH:44][CH:45]2[CH2:50][CH2:49][C:48](=[O:51])[CH:47]([O:52][CH3:53])[CH2:46]2)[CH:7]([CH3:55])[CH:6]([O:56][Si](C(C)C)(C(C)C)C(C)C)[CH2:5][C:4]1=[O:67])[CH3:2].C1C=CN=CC=1.F>O1CCCC1>[CH2:1]([CH:3]1[CH:29]=[C:28]([CH3:30])[CH:27]([F:31])[CH:26]([CH3:32])[CH2:25][CH:24]([O:33][CH3:34])[CH:23]2[O:35][C:19]([OH:39])([CH:20]([CH3:38])[CH2:21][CH:22]2[O:36][CH3:37])[C:18](=[O:40])[C:17](=[O:41])[N:16]2[CH:11]([CH2:12][CH2:13][CH2:14][CH2:15]2)[C:10](=[O:42])[O:9][CH:8]([C:43]([CH3:54])=[CH:44][CH:45]2[CH2:50][CH2:49][C:48](=[O:51])[CH:47]([O:52][CH3:53])[CH2:46]2)[CH:7]([CH3:55])[CH:6]([OH:56])[CH2:5][C:4]1=[O:67])[CH3:2]

Participants

5

Reactant 3

HCID 64774Pyridine, hydrofluoride (1:1)HCID 57254734HCID 57254734, compoundHCID 178435178HCID 178435178, compound

Product 1

HCID 57305705HCID 57305705, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 17-ethyl-20-fluoro-1-hydroxy-12-[2'-(3"-methoxy-4"-oxocyclohexyl)-1'-methylvinyl]-14-triisopropylsilyloxy-23,25-dimethoxy-13,19,21,27-tetramethyl-11,18-dioxa-4-azatricyclo[22.3.1.04,9 ]-octacos-18-ene-2,3,10, 16-tetraone from Example 23 (870 mg) in tetrahydrofuran (20 ml) contained in a polypropylene vial is added 4 ml of an HF-pyridine solution in tetrahydrofuran and the mixture was stirred at room temperature. 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-4b21bf1be65f41b88a34c6c7e5170697
Source dataset
uspto-grants-1993_02
Patent number
US05189042

Reaction notes

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