Sulfuric Acid → HCID 13565843, compound

HRID 1198596Notes

Reaction equation

HRID 1198596 reaction equation
[CH:1]1([N:4]([CH:23]=[C:24]([C:30]([O:32]CC)=O)[C:25]([O:27][CH2:28][CH3:29])=[O:26])[C:5]2[CH:10]=[CH:9][C:8]([F:11])=[C:7]([N:12]3[CH2:17][CH2:16][N:15]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:14][CH2:13]3)[N:6]=2)[CH2:3][CH2:2]1.S(=O)(=O)(O)O>C(OC(=O)C)(=O)C>[CH:1]1([N:4]2[C:5]3[C:10](=[CH:9][C:8]([F:11])=[C:7]([N:12]4[CH2:17][CH2:16][N:15]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:14][CH2:13]4)[N:6]=3)[C:30](=[O:32])[C:24]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:23]2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 13823372HCID 13823372, compound

Product 1

HCID 13565843HCID 13565843, compoundYield 19.3%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

A solution of 2.3 g (4.8 mmole) of [[cyclopropyl[6-[4-(ethoxycarbonyl)-1-piperazinyl]-5 -fluoro-2-pyridinyl]amino]methylene]propanedioic acid, diethyl ester, in 15 mL of acetic anhydride was treated dropwise with 5 mL of 98% sulfuric acid keeping the temperature 55°-60° C. When the addition was complete, the reaction was stirred for one hour and poured onto 50 g of ice. The aqueous suspension was extracted with chloroform, the chloroform layer washed with water, dried over magnesium sulfate, filtered, and evaporated in vacuo. The residue was triturated with several portions of ethanol/toluene which were also removed in vacuo to give 0.4 g of the title compound, mp 184°-186° C. An additional 0.5 g of product could be obtained by concentrating the original aqueous fraction, mp 184°-186° C.

Workup

  1. additionWhen the addition
  2. extractionThe aqueous suspension was extracted with chloroform
  3. washthe chloroform layer washed with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe residue was triturated with several portions of ethanol/toluene which
  8. customwere also removed in vacuo

Sources & evidence

ORD record
ord-4571addaa8384a13a25e852ed81fcd8c
Source dataset
uspto-grants-1994_01
Patent number
US05281612

Reaction notes

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