Acetic Acid → HCID 25061554, compound

HRID 1673219Notes

Reaction equation

HRID 1673219 reaction equation
Br[C:2]1([CH3:32])[C:25]2([CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)[O:24][C:5]2=[N:6][C:7]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[Cl:23])=[C:8]([C:10]3[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=3)[CH:9]=[C:4]2[C:3]1=[O:31].CC(O)=O>CCOC(C)=O.[Zn]>[Cl:23][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[C:7]1[N:6]=[C:5]2[O:24][C:25]3([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]3)[CH:2]([CH3:32])[C:3](=[O:31])[C:4]2=[CH:9][C:8]=1[C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 67019918HCID 67019918, compound

Product 1

HCID 25061554HCID 25061554, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8857Ethyl AcetateSolvent

Procedure

The product of Step B (20 mg, 0.037 mmol) was dissolved in EtOAc (1 mL) and AcOH (1 mL) and zinc (5 mg) were added. The reaction was stirred at rt for 10 min and concentrated. The residue was redissolved in CH2Cl2 and purified directly by silica gel flash chromatography gradient eluted with 0-15% EtOAc in hexane to afford the title compound. (LC-2) HPLC/MS: 452.4 (M+1), 545.4 (M+3); Rt=4.30 min.

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue was redissolved in CH2Cl2
  3. custompurified directly by silica gel flash chromatography gradient
  4. washeluted with 0-15% EtOAc in hexane

Sources & evidence

ORD record
ord-aecb9d4037874f079d5ae1748025ec32
Source dataset
uspto-grants-2011_08
Patent number
US07999107B2

Reaction notes

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