Hydrochloric Acid → HCID 22624299, compound

HRID 279063Notes

Reaction equation

HRID 279063 reaction equation
C(C([NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]2[CH:19]=[CH:18][C:17]([CH2:20][C:21]([O:23]CC)=[O:22])=[CH:16][C:15]=2[O:26][CH:27]([CH3:29])[CH3:28])[N:9]=1)=O)(C)(C)C.[OH-].[Na+].Cl>C(O)C>[CH:27]([O:26][C:15]1[CH:16]=[C:17]([CH2:20][C:21]([OH:23])=[O:22])[CH:18]=[CH:19][C:14]=1[C:10]1[N:9]=[C:8]([NH2:7])[CH:13]=[CH:12][CH:11]=1)([CH3:29])[CH3:28]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 22624291HCID 22624291, compound

Product 1

HCID 22624299HCID 22624299, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a 100 mL round-bottomed flask equipped with condenser and N2 inlet were added 577 mg (1.56 mmol) N-t-butylcarbonyl-6-(2-isopropoxy-4-carboethoxymethylphenyl)-pyridin-2-ylamine and 10 mL ethanol. The solution was heated to reflux, and 30 mL of a 10% aqueous sodium hydroxide solution added dropwise, and refluxing continued for 1 hour. The solution was cooled, and the pH adjusted at 0° C. with 1 N hydrochloric acid to pH 4-5, then extracted with methylene chloride, ethyl acetate, and acetonitrile/ethyl acetate. The combined organic layers were dried and evaporated to give a foam, 449 mg (98%).

Workup

  1. customTo a 100 mL round-bottomed flask equipped with condenser and N2 inlet
  2. temperatureThe solution was heated
  3. temperatureto reflux
  4. temperaturerefluxing
  5. temperatureThe solution was cooled
  6. extractionextracted with methylene chloride, ethyl acetate, and acetonitrile/ethyl acetate
  7. customThe combined organic layers were dried
  8. customevaporated
  9. customto give a foam, 449 mg (98%)

Sources & evidence

ORD record
ord-9b9f24dfdb304631a60a2b14ef67e1f2
Source dataset
uspto-grants-2002_03
Patent number
US06362195B1

Reaction notes

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