HCID 14677666, compound → HCID 14677667, compound

HRID 2073600Notes

Reaction equation

HRID 2073600 reaction equation
[Cl:1][C:2]1[C:14]([S:15](=[O:20])(=[O:19])[N:16]([CH3:18])[CH3:17])=[CH:13][C:5]2[CH:6]=[C:7]([C:9]([O:11]C)=[O:10])[O:8][C:4]=2[C:3]=1[Cl:21]>C(#N)C.O>[Cl:1][C:2]1[C:14]([S:15](=[O:19])(=[O:20])[N:16]([CH3:17])[CH3:18])=[CH:13][C:5]2[CH:6]=[C:7]([C:9]([OH:11])=[O:10])[O:8][C:4]=2[C:3]=1[Cl:21]

Participants

4

Reactant 1

HCID 14677666HCID 14677666, compound

Product 1

HCID 14677667HCID 14677667, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a hot solution of 582 mg (1.653 mmol) of methyl ester obtained in Example 1 in 15 ml of acetonitrile is added 1.7 ml (1.7 mmol) of aqueous N-NaOH solution and the mixture is stirred for 6 hours. Another 1.7 ml (1.7 mmol) of aqueous N-NaOH solution is added thereto and the reaction mixture is further stirred at room temperature for 24 hours. The precipitated crystals are collected by filtration and washed with a small amount of acetonitrile. The filtrates and washings are gathered and evaporated under reduced pressure to give a residue, which is dissolved in water and washed with methylene chloride. The previously obtained crystals are suspended in the aqueous layer, acidified with dil. hydrochloric acid, and extracted with ethyl acetate. The organic layer is washed with water, dried over anhydrous sodium sulfate, and evaporated under reduced pressure to leave a residue, which is recrystallized from ethyl acetate/hexane to give 458 mg (Yield 82.0%) of the objective compound (A'-1a), m.p. 242°-245° C.

Workup

  1. stirringthe reaction mixture is further stirred at room temperature for 24 hours
  2. filtrationThe precipitated crystals are collected by filtration
  3. washwashed with a small amount of acetonitrile
  4. customevaporated under reduced pressure
  5. customto give a residue, which
  6. washwashed with methylene chloride
  7. extractionextracted with ethyl acetate
  8. washThe organic layer is washed with water
  9. dry with materialdried over anhydrous sodium sulfate
  10. customevaporated under reduced pressure
  11. customto leave a residue, which
  12. customis recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-e25d0e0e68464ddaa0d4d456769d5317
Source dataset
uspto-grants-1990_04
Patent number
US04918206

Reaction notes

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