HCID 86707914, compound → HCID 58573987, compound

HRID 932282Notes

Reaction equation

HRID 932282 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:8]([CH2:24][CH:25]=[CH2:26])[C:9](=[N:17][S@@:18]([C:20]([CH3:23])([CH3:22])[CH3:21])=[O:19])[C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)[CH:5]=[CH:6][CH:7]=1.[CH3:27][Li]>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:8]([CH2:24][CH:25]=[CH2:26])[C@:9]([NH:17][S@@:18]([C:20]([CH3:21])([CH3:22])[CH3:23])=[O:19])([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)[CH3:27])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 86707914HCID 86707914, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 58573987HCID 58573987, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (R)—N—((R)-2-(3-chlorophenyl)-1-(4-chlorophenyl)pent-4-enylidene)-2-methylpropane-2-sulfinamide (Example 418, Step B, 9.97 g, 24.41 mmol) in THF (98 ml) was cooled to −78° C. Methyllithium (1.6M in ether, 16.78 ml, 26.9 mmol) was added over a period of six min. The reaction was removed from the cold bath and diluted with 500 mL ether and quenched with 150 mL of saturated aqueous ammonium chloride solution. The organic layer was separated and washed with brine, then dried with anhydrous magnesium sulfate and concentrated to afford a colorless oil. The crude material was adsorbed onto a plug of silica gel and purified by chromatography through (3×80 g) RediSep® pre-packed silica gel column (Teledyne Isco, Lincoln, Nebr.), eluting with 30% ethyl acetate in hexane. Fractions containing the desired product, eluting as the bottom spot on silica gel TLC in hexane/ethyl acetate, were combined and concentrated under reduced pressure to provide the title compound as a glass.

Workup

  1. customThe reaction was removed from the cold bath
  2. additiondiluted with 500 mL ether
  3. customquenched with 150 mL of saturated aqueous ammonium chloride solution
  4. customThe organic layer was separated
  5. washwashed with brine
  6. dry with materialdried with anhydrous magnesium sulfate
  7. concentrationconcentrated
  8. customto afford a colorless oil
  9. custompurified by chromatography through (3×80 g) RediSep® pre-packed silica gel column (Teledyne Isco, Lincoln, Nebr.)
  10. washeluting with 30% ethyl acetate in hexane
  11. additionFractions containing the desired product
  12. washeluting as the bottom spot on silica gel TLC in hexane/ethyl acetate
  13. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0e9ffafb1f744d68a94051fb606fdb7f
Source dataset
uspto-grants-2016_03
Patent number
US09296736B2

Reaction notes

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