Acetic Acid → HCID 178470463, compound

HRID 1774516

Reaction equation

HRID 1774516 reaction equation
[CH3:1][CH:2]([C:8](=O)[C:9]([O:11][CH2:12][CH3:13])=[O:10])[C:3]([O:5]CC)=O.C(O)(=O)C.Cl.Cl.[CH2:21]([O:23][C:24]1[CH:32]=[C:31]([F:33])[C:27]([CH2:28][NH:29][NH2:30])=[C:26]([F:34])[CH:25]=1)[CH3:22]>O1CCOCC1>[CH2:21]([O:23][C:24]1[CH:25]=[C:26]([F:34])[C:27]([CH2:28][N:29]2[C:3]([OH:5])=[C:2]([CH3:1])[C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[N:30]2)=[C:31]([F:33])[CH:32]=1)[CH3:22]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 97750Butanedioic acid, 2-methyl-3-oxo-, 1,4-diethyl esterHCID 89647959(4-Ethoxy-2,6-difluorobenzyl)hydrazine dihydrochloride

Product 1

HCID 178470463HCID 178470463, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

4.65 g of diethyl 2-methyl-3-oxobutanedioate (23.0 mmol, 1.00 eq.) were dissolved in 100 mL of dry dioxane under argon atmosphere. 2.1 mL of glacial acetic acid and 6.32 g of (4-ethoxy-2,6-difluorobenzyl)hydrazine dihydrochloride (23.00 mmol, 1.00 eq.) were added. The mixture was stirred for 16 hours at 90° C. bath temperature. The reaction mixture was evaporated in vacuo. The residue was stirred with ethyl acetate. The resulting suspension was filtered off and washed with ethyl acetate. The filter cake was dried in vacuo at 40° C. The filtrate was concentrated in vacuo and purified by flash chromatography (hexane/ethyl acetate-gradient with hexane 0-100%). The filter cake and the received purified compound of the flash chromatography were stirred together in ethyl acetate, filtered off and provided 3.95 g (11.3 mmol, 49%) of the analytically pure target compound.

Workup

  1. customThe reaction mixture was evaporated in vacuo
  2. stirringThe residue was stirred with ethyl acetate
  3. filtrationThe resulting suspension was filtered off
  4. washwashed with ethyl acetate
  5. customThe filter cake was dried in vacuo at 40° C
  6. concentrationThe filtrate was concentrated in vacuo
  7. custompurified by flash chromatography (hexane/ethyl acetate-gradient with hexane 0-100%)
  8. customThe filter cake and the received purified compound of the flash chromatography
  9. stirringwere stirred together in ethyl acetate
  10. filtrationfiltered off
  11. customprovided 3.95 g (11.3 mmol, 49%) of the analytically pure target compound

Sources & evidence

ORD record
ord-05e423e65cc346d39ac5e5cb6ddf2168
Source dataset
uspto-grants-2016_02
Patent number
US09260412B2

Linked notes

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