Water → HCID 67170480, compound

HRID 545106Notes

Reaction equation

HRID 545106 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([CH:19]=[CH:20][C:21]=1[Cl:22])[CH2:6][N:7]1[CH2:12][CH2:11][O:10][C@@H:9]([CH2:13][NH:14][C:15](=[O:18])[CH2:16]Cl)[CH2:8]1.[CH2:23]([O:25][C:26]([C:28]1[N:29]=[C:30]([SH:33])[S:31][CH:32]=1)=[O:27])[CH3:24].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[Cl:2][C:3]1[CH:4]=[C:5]([CH:19]=[CH:20][C:21]=1[Cl:22])[CH2:6][N:7]1[CH2:12][CH2:11][O:10][C@@H:9]([CH2:13][NH:14][C:15](=[O:18])[CH2:16][S:33][C:30]2[S:31][CH:32]=[C:28]([C:26]([O:25][CH2:23][CH3:24])=[O:27])[N:29]=2)[CH2:8]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 67169608HCID 67169608, compoundHCID 178470113HCID 178470113, compound

Product 1

HCID 67170480HCID 67170480, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The resultant product (776 mg) of (1-2) and the resultant product (379 mg) of (1-3) were dissolved in dimethylformamide (6 mL), potassium carbonate (829 mg) was added, and the mixture was stirred overnight at room temperature. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography using a mixed solvent of chloroform and methanol as an eluent. The solvent was evaporated from the eluent to give the title compound (850 mg) as a pale-yellow oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography
  6. customThe solvent was evaporated from the eluent

Sources & evidence

ORD record
ord-edd85d36a50f4a5cb837aabd0e0ef1b9
Source dataset
uspto-grants-2011_05
Patent number
US07935700B2

Reaction notes

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