Ammonium Chloride → HCID 86709277, compound

HRID 517295Notes

Reaction equation

HRID 517295 reaction equation
[Si]([O:8][CH2:9][CH2:10][NH:11][S:12]([C:15]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[CH2:16])(=[O:14])=[O:13])(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[NH4+].[Cl-]>O1CCCC1>[C:17]1([CH:15]2[S:12](=[O:14])(=[O:13])[NH:11][CH2:10][CH2:9][O:8][CH2:16]2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 2724141Tetrabutylammonium FluorideHCID 86709276HCID 86709276, compound

Product 1

HCID 86709277HCID 86709277, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-(2-((Tert-butyldimethylsilyl)oxy)ethyl)-1-phenylethenesulfonamide (717 mg, 2.1 mmol) in tetrahydrofuran (7 mL) at 0° C. was added tetrabutylammonium fluoride (1.0 M in THF) (2.2 mL, 2.2 mmol) dropwise and the reaction was stirred at room temperature for 16 hours. Saturated NH4Cl was then added and the product was extracted with dichloromethane (×2), dried with MgSO4, concentrated and purified by silica gel column chromatography (0-100% EtOAc in heptane) to give 3-phenyl-1,4,5-oxathiazepane 4,4-dioxide (401 mg, 84% yield). (24 g, 70% yield). LCMS (ESI), m/z, 228. [M+H]+. (Reference: P. Hansen, et al. Org. Lett. 2008, 2951).

Workup

  1. extractionthe product was extracted with dichloromethane (×2)
  2. dry with materialdried with MgSO4
  3. concentrationconcentrated
  4. custompurified by silica gel column chromatography (0-100% EtOAc in heptane)

Sources & evidence

ORD record
ord-96469ba0f4cb44f78c32a1bf1f1148d9
Source dataset
uspto-grants-2015_08
Patent number
US09115101B2

Reaction notes

Loading…