(Diethylamino)sulfur trifluoride → HCID 9836204, compound

HRID 1797219Notes

Reaction equation

HRID 1797219 reaction equation
C(N(S(F)(F)[F:7])CC)C.[F:10][C:11]1[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[CH:13][C:12]=1[C:19](O)([CH3:28])[CH2:20][NH:21][S:22]([CH:25]([CH3:27])[CH3:26])(=[O:24])=[O:23]>C(Cl)Cl>[F:7][C:19]([C:12]1[CH:13]=[CH:14][C:15]([O:17][CH3:18])=[CH:16][C:11]=1[F:10])([CH3:28])[CH2:20][NH:21][S:22]([CH:25]([CH3:27])[CH3:26])(=[O:24])=[O:23]

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 23567039Propane-2-sulfonic acid [2-(2-fluoro-4-methoxyphenyl)-2-hydroxy-propyl]-amide

Product 1

HCID 9836204HCID 9836204, compoundYield 64.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A dry CH2Cl2 solution (10 mL) of (diethylamino)sulfur trifluoride (DAST) (0.419 mL, 3.17 mmol) was cooled to −78° C. while stirring under N2. A CH2Cl2 solution (5 mL) of propane-2-sulfonic acid [2-(2-fluoro-4-methoxyphenyl)-2-hydroxy-propyl]-amide (0.79 g, 2.64 mmol) was added dropwise via syringe and the reaction was immediately brought to 0° C. The reaction was quenched with water and diluted with diethyl ether. The organic layer was separated and washed with water and saturated NaCl solution, dried (MgSO4), filtered, and concentrated to a yellow oil. The crude residue was purified by silica gel chromatography, eluting with 30% ethyl acetate/hexanes, to provide the final title compound, propane-2-sulfonic acid [2-fluoro-2-(2-fluoro-4-methoxy-phenyl)-propyl]-amide, (0.52 g, 64%) as a light yellow oil.

Workup

  1. customwas immediately brought to 0° C
  2. customThe reaction was quenched with water
  3. additiondiluted with diethyl ether
  4. customThe organic layer was separated
  5. washwashed with water and saturated NaCl solution
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated to a yellow oil
  9. customThe crude residue was purified by silica gel chromatography
  10. washeluting with 30% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-e978195729534fa4b2c08cc70534c81d
Source dataset
uspto-grants-2006_04
Patent number
US07034045B1

Reaction notes

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