Ammonium Chloride → HCID 23144557, compound

HRID 337441Notes

Reaction equation

HRID 337441 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[S:10][C:11]([C:19](N(OC)C)=[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].[C:25]1([Mg]Cl)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[Cl-].[NH4+]>C1COCC1>[C:19]([C:11]1[S:10][C:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[N:13][C:12]=1[C:14]1[O:15][CH:16]=[CH:17][CH:18]=1)(=[O:20])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 23144610HCID 23144610, compoundHCID 178478979HCID 178478979, compound

Product 1

HCID 23144557HCID 23144557, compoundYield 55.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Compound 134 (10.7 g, 30.3 mmol) was dissolved in THF (240 ml), and a THF solution of 2.0 mol/L phenylmagnesium chloride (60.6 mL, 121 mmol) was added thereto at 0° C. in an atmosphere of argon, followed by stirring at room temperature for 2 hours. The reaction mixture was poured into a saturated aqueous solution of ammonium chloride, followed by extraction with ethyl acetate. 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 (hexane:ethyl acetate=3:1) to afford the entitled Compound 135 (6.18 g, 55%).

Workup

  1. customat 0° C.
  2. extractionfollowed by extraction with ethyl acetate
  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 (hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-a94f1e8d11064da993b526739475c8ba
Source dataset
uspto-grants-2014_11
Patent number
US08889718B2

Reaction notes

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