Acetic Acid → HCID 57893425, compound

HRID 1822375Notes

Reaction equation

HRID 1822375 reaction equation
C(O[C:4](=[O:22])[C:5](=[N:12][NH:13][C:14](=[O:21])[CH2:15][C:16]([O:18]CC)=O)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)C.[NH:23](C(=O)CC(OCC)=O)N.[C:33]([C:41]([O:43]CC)=[O:42])(=O)C1C=CC=CC=1.C(O)(=O)C.S([O-])([O-])(=O)=O.[Mg+2]>ClCCl>[OH:22][C:4]1[C:5]([C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=2)=[N:12][NH:13][C:14](=[O:21])[C:15]=1[C:16]([NH:23][CH2:33][C:41]([OH:43])=[O:42])=[O:18]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 15349Ethyl benzoylformateHCID 24083Sulfuric acid magnesium salt (1:1)HCID 252897Ethyl 3-hydrazino-3-oxopropionateHCID 86623016HCID 86623016, compound

Product 1

HCID 57893425HCID 57893425, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethyl 3-{2-[2-(ethyloxy)-2-oxo-1-phenylethylidene]hydrazino}-3-oxopropanoate. A mixture of ethyl 3-hydrazino-3-oxopropionate (1.46 g, 10.0 mmol), ethyl benzoylformate (2.14 g, 12.0 mmol), acetic acid (0.5 mL, 8.3 mmol) and dichloromethane (10 mL) was stirred at room temperature with excess anhydrous magnesium sulfate for 20 h, then filtered and the cake washed with ethyl acetate. The filtrate was evaporated under reduced pressure, azeotroped 3 times with toluene and chromatographed (silica gel, 10-3-% ethyl acetate/hexane) to give the title compound (0.773 g, 25%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.15 (t, J=7.07 Hz, 3H) 1.30 (t, J=7.07 Hz, 3H) 3.74 (s, 2H) 4.08 (q, J=7.07 Hz, 2H) 4.40 (q, J=7.18 Hz, 2H) 7.42-7.49 (m, 3H) 7.55-7.59 (m, 2H) 11.57 (s, 1H).

Workup

  1. filtrationfiltered
  2. washthe cake washed with ethyl acetate
  3. customThe filtrate was evaporated under reduced pressure
  4. customazeotroped 3 times with toluene
  5. customchromatographed (silica gel, 10-3-% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-7a8fffe977af4262912cf4d160e8f898
Source dataset
uspto-grants-2009_10
Patent number
US07608621B2

Reaction notes

Loading…