Hexane → HCID 23144547, compound

HRID 337478Notes

Reaction equation

HRID 337478 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[S:10][C:11]([CH:19]=[O:20])=[C:12]([C:14]2[O:15][CH:16]=[CH:17][CH:18]=2)[N:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:21]([Li])[CH2:22][CH2:23][CH3:24].CCCCCC.[Cl-].[NH4+]>C1COCC1>[O:15]1[CH:16]=[CH:17][CH:18]=[C:14]1[C:12]1[N:13]=[C:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:2])[CH3:3])[S:10][C:11]=1[CH:19]([OH:20])[CH2:21][CH2:22][CH2:23][CH3:24]

Participants

6

Reactant 4

HCID 8058HexaneHCID 25517Ammonium ChlorideHCID 23144187HCID 23144187, compoundHCID 178418339Butyllithium

Product 1

HCID 23144547HCID 23144547, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Compound 92 (298 mg, 1.01 mmol) was dissolved in THF (10 mL), and a 1.59 mol/L solution of n-butyllithium in n-hexane (5.70 mL, 9.06 mmol) was added thereto in a stream of argon at −78° C., followed by stirring at room temperature for 2 hours. A saturated aqueous solution of ammonium chloride was added to the reaction mixture, followed by extraction with chloroform. The organic layer was dried over anhydrous magnesium sulfate, and then the solvent was distilled away under reduced pressure. The resulting residue was purified through silica gel column chromatography (hexane:ethyl acetate=3:1) to afford the entitled Compound 395 (224 mg, 63%).

Workup

  1. customat −78° C.
  2. extractionfollowed by extraction with chloroform
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled away under reduced pressure
  5. customThe resulting residue was purified through silica gel column chromatography (hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-42ecaa4fb6f04461a1ec0017cf25daf3
Source dataset
uspto-grants-2014_11
Patent number
US08889718B2

Reaction notes

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