2-Phenylacetophenone → 2-Tert-butyl-1,1-dioxo-5-[4-(3-oxo-2,3-diphenyl-propyl)-phenyl]-1lambda6-isothiazolidin-3-one

HRID 724629Notes

Reaction equation

HRID 724629 reaction equation
[C:1]1([C:7]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC(C)([O-])C.[K+].Br[CH2:23][C:24]1[CH:29]=[CH:28][C:27]([CH:30]2[S:34](=[O:36])(=[O:35])[N:33]([C:37]([CH3:40])([CH3:39])[CH3:38])[C:32](=[O:41])[CH2:31]2)=[CH:26][CH:25]=1>O1CCCC1>[C:37]([N:33]1[C:32](=[O:41])[CH2:31][CH:30]([C:27]2[CH:26]=[CH:25][C:24]([CH2:23][CH:9]([C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:7](=[O:8])[C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[CH:29][CH:28]=2)[S:34]1(=[O:36])=[O:35])([CH3:40])([CH3:38])[CH3:39]

Participants

5

Reactant 3

HCID 99482-PhenylacetophenoneHCID 23665647Potassium tert-butoxideHCID 587466605-(4-Bromomethyl-phenyl)-2-tert-butyl-1,1-dioxo-1lambda6-isothiazolidin-3-one

Product 1

HCID 587468382-Tert-butyl-1,1-dioxo-5-[4-(3-oxo-2,3-diphenyl-propyl)-phenyl]-1lambda6-isothiazolidin-3-oneYield 50%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

A solution of deoxybenzoin (62.6 mg, 0.32 mmol) in tetrahydrofuran (1.3 mL) was cooled to −78° C. and potassium tert-butoxide (0.15 mL, 0.15 mmol, 1.0 M in tetrahydrofuran) was added dropwise. The reaction mixture was stirred at −78° C. for 10 minutes and 4.19-A of Step 1 (115 mg, 0.32 mmol) in tetrahydrofuran (1.5 mL) was added dropwise. The reaction mixture was warmed to 25° C. and quenched with saturated ammonium chloride (15 mL) and extracted with ethyl acetate (2×30 mL). The combined organic extracts were washed with brine (15 mL), dried with sodium sulfate, filtered, and concentrated to a crude yellow oil which was purified by flash column chromatography to yield the desired product (75 mg, 50%). LCMS found for C28H29NO4SNa (M+Na)+: m/z=498.

Workup

  1. temperatureThe reaction mixture was warmed to 25° C.
  2. customquenched with saturated ammonium chloride (15 mL)
  3. extractionextracted with ethyl acetate (2×30 mL)
  4. washThe combined organic extracts were washed with brine (15 mL)
  5. dry with materialdried with sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated to a crude yellow oil which
  8. customwas purified by flash column chromatography

Sources & evidence

ORD record
ord-19ab1f46626b46c3bc85e1986d573501
Source dataset
uspto-grants-2006_11
Patent number
US07141596B2

Reaction notes

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