Hydrochloric Acid → HCID 23144537, compound

HRID 1361788Notes

Reaction equation

HRID 1361788 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][NH:23][C:22](=[O:26])[CH:21]=2)=[O:19])[S:9][C:10]=1[C:11]1[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=1.[H-].[Na+].[CH2:29](Br)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.Cl>CN(C=O)C.O>[CH2:29]([N:23]1[CH:24]=[CH:25][C:20]([C:18]([NH:17][C:8]2[S:9][C:10]([C:11]3[CH:12]=[CH:13][N:14]=[CH:15][CH:16]=3)=[C:6]([C:2]3[O:1][CH:5]=[CH:4][CH:3]=3)[N:7]=2)=[O:19])=[CH:21][C:22]1=[O:26])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 23144325HCID 23144325, compound

Product 1

HCID 23144537HCID 23144537, compoundYield 14%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Compound 112 (146 mg, 0.400 mmol) was dissolved in DMF (2 mL), 60% sodium hydride (35.2 mg, 0.880 mmol) was added thereto, followed by stirring at room temperature for 30 minutes. Benzyl bromide (0.0523 mL, 0.440 mmol) was added dropwise to the reaction mixture, followed by stirring overnight at room temperature. The reaction mixture was poured into water, and 1 mol/L hydrochloric acid was added thereto to adjust the pH to 7, 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 (chloroform:methanol=99:1) to afford the entitled Compound 113 (25.0 mg, 14%).

Workup

  1. stirringby stirring overnight at room temperature
  2. additionwas added
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled away under reduced pressure
  7. customThe resulting residue was purified through silica gel column chromatography (chloroform:methanol=99:1)

Sources & evidence

ORD record
ord-ac562a2061de4ff6acff2d4fa19ad5f1
Source dataset
uspto-grants-2011_02
Patent number
US07880013B2

Reaction notes

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