Water → HCID 70176329, compound

HRID 840357Notes

Reaction equation

HRID 840357 reaction equation
Cl[CH:2]([CH2:8][C:9]1[CH:14]=[C:13]([N:15]2[C:19](=[O:20])[C:18]3=[CH:21][CH:22]=[CH:23][CH:24]=[C:17]3[C:16]2=[O:25])[C:12]([F:26])=[CH:11][C:10]=1[Cl:27])[C:3]([O:5][CH2:6][CH3:7])=[O:4].C1CCN2C(=NCCC2)CC1.O>O1CCCC1>[Cl:27][C:10]1[CH:11]=[C:12]([F:26])[C:13]([N:15]2[C:19](=[O:20])[C:18]3=[CH:21][CH:22]=[CH:23][CH:24]=[C:17]3[C:16]2=[O:25])=[CH:14][C:9]=1[CH:8]=[CH:2][C:3]([O:5][CH2:6][CH3:7])=[O:4]

Participants

5

Reactant 3

HCID 962WaterHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 11338825HCID 11338825, compound

Product 1

HCID 70176329HCID 70176329, compoundYield 69.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In 20 ml of tetrahydofuran was dissolved 1.23 g of ethyl 2-chloro-3-(2-chloro-4-fluoro-5-phthalimidophenyl)propionate, and 0.69 g of 1,8-diazabicyclo[5.4.0]-7-undecene was slowly added thereto dropwise. After the addition, the stirring was continued at room temperature for 1.5 hours. Water was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed successively with water and a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (chloroform) to give 0.78 g of the title compound (No. 17 of Table 2).

Workup

  1. additionwas slowly added
  2. additionAfter the addition
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed successively with water
  5. dry with materiala saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (chloroform)

Sources & evidence

ORD record
ord-a31b27b7177d4e80ac7d60422688b642
Source dataset
uspto-grants-2002_04
Patent number
US06365753B1

Reaction notes

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