Potassium Carbonate → HCID 90384613, compound

HRID 1846409Notes

Reaction equation

HRID 1846409 reaction equation
[CH2:1]([NH:8][C:9]([C@H:11]1[CH2:20][C:19]23[CH2:21][CH2:22][C@:12]1([OH:36])[CH:13]1[O:30][C:28]4=[C:29]5[C@@:14]12[CH2:15][CH2:16][N:17]([CH2:32][CH:33]1[CH2:35][CH2:34]1)[C@@H:18]3[CH2:23][C:24]5=[CH:25][CH:26]=[C:27]4[OH:31])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[C:38]1[N:42]([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[N:41]=[N:40][N:39]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C(OCC)(=O)C>[CH2:1]([NH:8][C:9]([C@H:11]1[CH2:20][C:19]23[CH2:21][CH2:22][C@:12]1([OH:36])[CH:13]1[O:30][C:28]4=[C:29]5[C@@:14]12[CH2:15][CH2:16][N:17]([CH2:32][CH:33]1[CH2:34][CH2:35]1)[C@@H:18]3[CH2:23][C:24]5=[CH:25][CH:26]=[C:27]4[O:31][C:38]1[N:42]([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[N:41]=[N:40][N:39]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 842621H-Tetrazole, 5-chloro-1-phenyl-HCID 90384467HCID 90384467, compound

Product 1

HCID 90384613HCID 90384613, compoundYield 96.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Under an argon atmosphere, the compound 111 (2 g, 4.11 mmol) was dissolved in DMF (40 mL), the solution was added with 5-chloro-1-phenyl-1H-tetrazole (891 mg, 4.93 mmol), and potassium carbonate (1.42 g, 10.3 mmol), and the mixture was stirred at room temperature for 16 hours. The reaction mixture was diluted with ethyl acetate, and washed with saturated aqueous sodium hydrogencarbonate, water, and saturated brine. The organic layer was dried over anhydrous sodium sulfate, and then concentrated. The obtained crude product was purified by silica gel column chromatography to give the title compound 112 (2.5 g, 96%).

Workup

  1. washwashed with saturated aqueous sodium hydrogencarbonate, water, and saturated brine
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated
  4. customThe obtained crude product
  5. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-02dbda41db79461a9f0f6d68c0bdac40
Source dataset
uspto-grants-2015_02
Patent number
US08952030B2

Reaction notes

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