Ethyl Acetate → HCID 86648213, compound

HRID 1469645Notes

Reaction equation

HRID 1469645 reaction equation
[CH2:1]([O:3][C:4](=[O:10])[CH2:5][C:6]([NH:8][NH2:9])=[O:7])[CH3:2].[C:11](Cl)(=[O:14])[CH2:12][CH3:13].C(OCC)(=O)C>C1COCC1>[CH2:1]([O:3][C:4](=[O:10])[CH2:5][C:6](=[O:7])[NH:8][NH:9][C:11](=[O:14])[CH2:12][CH3:13])[CH3:2]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 62324Propionyl chlorideHCID 252897Ethyl 3-hydrazino-3-oxopropionate

Product 1

HCID 86648213HCID 86648213, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of hydrazinocarbonylacetic acid ethyl ester (1.0 g, 6.84 mmol) and diisopropypethylamine (1.77 g, 13.69 mmol) in THF (7 mL) is added a solution of propionyl chloride (633 mg, 6.84 mmol) in THF (2 mL) dropwise and the mixture is stirred at room temperature for 18 hours. The mixture is poured into ethyl acetate and is washed with aqueous 1M HCl and brine. The organic phase is dried over magnesium sulfate and the solvent is removed under reduced pressure to furnish 3-oxo-3-(N′-propionylhydrazino)-propionic acid ethyl ester. 1H-NMR (400 MHz, CDCl3); δ ppm 1.21 (t, 3H), 1.30 (t, 3H), 2.31 (q, 2H), 3.43 (s, 2H), 4.23 (q, 2H), 8.27 (s, 1H), 9.63 (s, 1H).

Workup

  1. washis washed with aqueous 1M HCl and brine
  2. dry with materialThe organic phase is dried over magnesium sulfate
  3. customthe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-90c4056ae5d04db892c02f8425c80268
Source dataset
uspto-grants-2015_04
Patent number
US09006249B2

Reaction notes

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