Hydrochloric Acid → HCID 21867462, compound

HRID 857344Notes

Reaction equation

HRID 857344 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[C:7]2[C:3]=1[C:4]([S:22][C:23]1[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=1)=[C:5]1[C:15](=[O:16])[CH:14](C(OCC)=O)[CH2:13][CH2:12][N:6]12.Cl.C([O-])(O)=O.[Na+]>CCO>[Br:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[C:7]2[C:3]=1[C:4]([S:22][C:23]1[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=1)=[C:5]1[C:15](=[O:16])[CH2:14][CH2:13][CH2:12][N:6]12

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 58760777HCID 58760777, compound

Product 1

HCID 21867462HCID 21867462, compoundYield 64.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of the ketoester of Step 3 (400 mg) in EtOH (10 mL) at r.t. was added 3 mL of concentrated HCl. The reaction mixture was stirred at reflux for 4 hours, cooled and poured into saturated aqueous NaHCO3. The aqueous layer was extracted with EtOAc and the combined organic layers were dried over Na2SO4 and concentrated. The residue was swished in EtOAc to provide 220 mg of the title compound as a yellow solid.

Workup

  1. temperatureat reflux for 4 hours
  2. temperaturecooled
  3. extractionThe aqueous layer was extracted with EtOAc
  4. dry with materialthe combined organic layers were dried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-3b56facb324d479e8366c4cad0c53593
Source dataset
uspto-grants-2006_12
Patent number
US07144913B2

Reaction notes

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