Ammonium Chloride → HCID 10292869, compound

HRID 2184402Notes

Reaction equation

HRID 2184402 reaction equation
[CH3:1][CH:2]([S:4]([NH:7][CH:8]1[CH2:12][CH2:11][CH2:10][C:9]1=[O:13])(=[O:6])=[O:5])[CH3:3].[O:14]([C:21]1[CH:26]=[CH:25][C:24]([Mg]Br)=[CH:23][CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[Cl-].[NH4+]>C1COCC1.O>[OH:13][C:9]1([C:24]2[CH:25]=[CH:26][C:21]([O:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:22][CH:23]=2)[CH2:10][CH2:11][CH2:12][CH:8]1[NH:7][S:4]([CH:2]([CH3:1])[CH3:3])(=[O:6])=[O:5]

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 22476614HCID 22476614, compound3×HCID 178419636HCID 178419636, compound

Product 1

HCID 10292869HCID 10292869, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Into a flame dried 250 mL 3 neck flask that was fitted with a thermometer and condenser, and while stirring at room temperature under a nitrogen atmosphere, 2-{[(methylethyl)sulfonyl]amino}cyclopentan-1-one (1.00 g, 4.9 mmol) in THF (40 mL) was added dropwise to 15 mL of 0.5 M 4-phenoxyphenylmagnesium bromide. The addition of 2-{[(methylethyl)sulfonyl]amino}cyclopentan-1-one was continued dropwise, keeping the temperature above 35° C. After the addition of 2-{[(methylethyl)sulfonyl]amino}cyclopentan-1-one was complete, the reaction was stirred overnight at room temperature. Enough saturated ammonium chloride in water was then added to precipitate salts and the organic layer was decanted off. The remaining salts were washed two times with ether and the combined organic layers were concentrated under reduced vacuum. The resulting semi-solid was taken into ethyl acetate, washed once with water, dried over potassium carbonate, filtered, and concentrated under reduced vacuum to yield 2.14 g of as a dark oil. This material was purified via silica gel chromatography employing the Water's Prep. 2000 while eluting with a solvent of hexane/ethyl acetate 7:3 to provide the title compound (540 mg) as a white solid. Ion spray M.S. 374.1 (M*−1). Calculated for C20H25NO4S: Theory: C, 63.98; H, 6.71; N, 3.73. Found: C, 63.70; H, 6.77; N, 3.55.

Workup

  1. dry with materialInto a flame dried 250 mL 3 neck flask that
  2. customwas fitted with a thermometer and condenser
  3. customthe temperature above 35° C
  4. stirringthe reaction was stirred overnight at room temperature
  5. customto precipitate salts
  6. customthe organic layer was decanted off
  7. washThe remaining salts were washed two times with ether
  8. concentrationthe combined organic layers were concentrated under reduced vacuum
  9. washwashed once with water
  10. dry with materialdried over potassium carbonate
  11. filtrationfiltered
  12. concentrationconcentrated under reduced vacuum
  13. customto yield 2.14 g of as a dark oil
  14. customThis material was purified via silica gel chromatography
  15. wash2000 while eluting with a solvent of hexane/ethyl acetate 7:3

Sources & evidence

ORD record
ord-264e8d92f00c4afa92bef229fb27ebfd
Source dataset
uspto-grants-2005_05
Patent number
US06900353B2

Reaction notes

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