Ammonium Chloride → HCID 23144545, compound

HRID 1967802Notes

Reaction equation

HRID 1967802 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[N:7]=[C:8]([NH:17][C:18]([C:20]2[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=2)=[O:19])[S:9][C:10]=1[C:11](=[O:16])N(OC)C.[CH2:26]([Mg]Br)[CH3:27].[Cl-].[NH4+]>C1COCC1>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[N:7]=[C:8]([NH:17][C:18]([C:20]2[CH:21]=[CH:22][N:23]=[CH:24][CH:25]=2)=[O:19])[S:9][C:10]=1[C:11](=[O:16])[CH2:26][CH3:27]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 23144082HCID 23144082, compoundHCID 178418443HCID 178418443, compound

Product 1

HCID 23144545HCID 23144545, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Compound 98 (200 mg, 0.559 mmol) was suspended in THF (2 mL), and a 0.89 mol/L solution of ethylmagnesium bromide (2.00 mL, 1.78 mmol) in THF was added thereto under ice-cooling, followed by stirring overnight at room temperature. A saturated aqueous solution of ammonium chloride was added to the reaction mixture, followed by extraction with a mixed solvent (4:1) of chloroform and 2-propanol. The organic layer was washed with a saturated aqueous solution of sodium chloride and 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 (chloroform:methanol=200:1) to afford the entitled Compound 381 (27.2 mg, 15%) as a pale yellow solid.

Workup

  1. temperatureunder ice-cooling
  2. extractionfollowed by extraction with a mixed solvent (4:1) of chloroform and 2-propanol
  3. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled away under reduced pressure
  6. customThe resulting residue was purified through silica gel column chromatography (chloroform:methanol=200:1)

Sources & evidence

ORD record
ord-4ca58adee2ab46c086393c4e96974961
Source dataset
uspto-grants-2013_04
Patent number
US08420827B2

Reaction notes

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