Potassium Carbonate → HCID 59676997, compound

HRID 2104455Notes

Reaction equation

HRID 2104455 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([C:12]([NH:14][C@@H:15]1[CH2:19][NH:18][CH2:17][C@H:16]1[NH:20][C:21]([C:23]1[S:24][C:25]3[CH2:26][N:27]([CH3:32])[CH2:28][CH2:29][C:30]=3[N:31]=1)=[O:22])=[O:13])=[CH:6]2.C(=O)([O-])[O-].[K+].[K+].Br[CH2:40][C:41]([O:43][CH3:44])=[O:42]>CN(C)C=O.C(OCC)(=O)C>[Cl:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([C:12]([NH:14][C@H:15]1[C@H:16]([NH:20][C:21]([C:23]3[S:24][C:25]4[CH2:26][N:27]([CH3:32])[CH2:28][CH2:29][C:30]=4[N:31]=3)=[O:22])[CH2:17][N:18]([CH2:40][C:41]([O:43][CH3:44])=[O:42])[CH2:19]1)=[O:13])=[CH:6]2

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 67056761HCID 67056761, compound

Product 1

HCID 59676997HCID 59676997, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

The compound (230 mg) obtained in Example 95 and potassium carbonate (90 mg) were dissolved in N,N-dimethylformamide (4.6 mL), and the mixture was cooled with ice. Methyl bromoacetate (0.062 mL) was added, and the resultant mixture was stirred for 45 minutes. The reaction mixture was diluted with ethyl acetate, washed with water and saturated brine and then dried over sodium sulfate anhydrate, and the solvent was distilled away under reduced pressure. The resultant residue was purified by silica gel thin layer chromatography (chloroform:methanol=10:1) and powdered with methanol-water to give the title compound (190 mg).

Workup

  1. temperaturethe mixture was cooled with ice
  2. washwashed with water and saturated brine
  3. dry with materialdried over sodium sulfate anhydrate
  4. distillationthe solvent was distilled away under reduced pressure
  5. customThe resultant residue was purified by silica gel thin layer chromatography (chloroform:methanol=10:1)

Sources & evidence

ORD record
ord-9ba307b8eb8e47e596dc5cf3e5ed3557
Source dataset
uspto-grants-2009_08
Patent number
US07576135B2

Reaction notes

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