Potassium bisulfate → HCID 12073624, compound

HRID 561765Notes

Reaction equation

HRID 561765 reaction equation
[Si]([O:18][CH2:19][C@H:20]1[C@@H:24]([F:25])[CH2:23][C@H:22]([O:26][CH:27]2[CH2:32][CH2:31][CH2:30][CH2:29][O:28]2)[C@@H:21]1[CH2:33]/[CH:34]=[CH:35]\[CH2:36][CH2:37][CH2:38][C:39]([O:41][CH:42]([CH3:44])[CH3:43])=[O:40])(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-].OS([O-])(=O)=O.[K+]>C1COCC1>[F:25][C@H:24]1[CH2:23][C@H:22]([O:26][CH:27]2[CH2:32][CH2:31][CH2:30][CH2:29][O:28]2)[C@H:21]([CH2:33]/[CH:34]=[CH:35]\[CH2:36][CH2:37][CH2:38][C:39]([O:41][CH:42]([CH3:44])[CH3:43])=[O:40])[C@H:20]1[CH2:19][OH:18]

Participants

5

Reactant 3

HCID 516920Potassium bisulfateHCID 2724141Tetrabutylammonium FluorideHCID 57857047HCID 57857047, compound

Product 1

HCID 12073624HCID 12073624, compoundYield 64.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirring solution consisting of (Z)-isopropyl 7-((1R,2S,3S,5S)-2-((tert-butyldiphenylsilyloxy)methyl)-3-fluoro-5-(tetrahydro-2H-pyran-2-yloxy)cyclopentyl)hept-5-enoate (prepared in Step E, 2.7 g, 52 mmol) in anhydrous THF (500 mL) was slowly added a solution consisting of 1 M TBAF in THF (157 mL). The reaction mixture was stirred for 4 hours, monitoring by TLC. The reaction mixture was acidified with 5% KHSO4, extracted into ethyl acetate, washed with brine, and dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude product was purified on silica gel, eluted with hexanes-ethyl acetate (3:1) to afford the title intermediate 12.94 g, 64%).

Workup

  1. additionwas slowly added a solution
  2. extractionextracted into ethyl acetate
  3. washwashed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified on silica gel
  8. washeluted with hexanes-ethyl acetate (3:1)

Sources & evidence

ORD record
ord-6d3cf8b067f1446790b491ca76cddd0d
Source dataset
uspto-grants-2011_11
Patent number
US08063240B2

Reaction notes

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