Ammonium Chloride → HCID 178519825, compound

HRID 1913526Notes

Reaction equation

HRID 1913526 reaction equation
[Si]([O:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([N:15]2[CH:19]=[C:18]([CH:20]=[O:21])[N:17]=[CH:16]2)[CH2:11][CH2:10]1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Cl-].[NH4+]>O1CCCC1>[OH:8][C@H:9]1[CH2:10][CH2:11][C@H:12]([N:15]2[CH:19]=[C:18]([CH:20]=[O:21])[N:17]=[CH:16]2)[CH2:13][CH2:14]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 2724141Tetrabutylammonium FluorideHCID 178455352HCID 178455352, compound

Product 1

HCID 178519825HCID 178519825, compoundYield 73.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

The compound (540 mg) obtained in Step 2 of this Reference Example was dissolved in tetrahydrofuran (8 mL). To this solution, a solution of tetrabutylammonium fluoride in tetrahydrofuran (1.0 M, 2.62 mL) was added, and the mixture was stirred at room temperature for 8 hours. To the reaction solution, saturated aqueous ammonium chloride was added, and organic matter was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and filtered, and the solvent was distilled off under reduced pressure to obtain a crude product. This crude product was purified by diol-bonded silica gel column chromatography (eluting solvent: hexane/ethyl acetate=1/1-ethyl acetate) to obtain the title compound (250 mg).

Workup

  1. extractionorganic matter was extracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. distillationthe solvent was distilled off under reduced pressure
  5. customto obtain a crude product
  6. customThis crude product was purified by diol-
  7. washsilica gel column chromatography (eluting solvent: hexane/ethyl acetate=1/1-ethyl acetate)

Sources & evidence

ORD record
ord-d51b1b7f3a2440d39b101467ef12b60e
Source dataset
uspto-grants-2013_12
Patent number
US08609710B2

Reaction notes

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