Water → Acetic Acid 2-(N'-benzyloxycarbonyl-hydrazino)-2-oxo-ethyl Ester

HRID 34051

Reaction equation

HRID 34051 reaction equation
[CH2:1]([O:8][C:9]([NH:11][NH2:12])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:20]([O:23][CH2:24][C:25](Cl)=[O:26])(=[O:22])[CH3:21].O>ClCCl>[CH2:1]([O:8][C:9]([NH:11][NH:12][C:25](=[O:26])[CH2:24][O:23][C:20](=[O:22])[CH3:21])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 26297Acetoxyacetyl chlorideHCID 79242Benzyl carbazate

Product 1

HCID 59796922Acetic Acid 2-(N'-benzyloxycarbonyl-hydrazino)-2-oxo-ethyl Ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2.04 g of hydrazine carboxylic acid benzyl ester in 40 mL of dichloromethane was added 2.57 mL of triethylamine. Under ice cooling, a solution of 1.32 mL of acetoxyacetylchloride in 20 mL of dichloromethane was added dropwise over 25 minutes, and stirred at room temperature for 1 hour. The reaction solution was added with water, extracted with ethyl acetate, and the resultant organic layer was washed with 1N hydrochloric acid, saturated aqueous sodium hydrogen carbonate and saturated brine, and then dried over magnesium sulfate. The solvent was evaporated, and the resulting solid product was washed with diethyl ether and collected by filtration, to give 1.92 g of the title compound as white crystals.

Workup

  1. extractionextracted with ethyl acetate
  2. washthe resultant organic layer was washed with 1N hydrochloric acid, saturated aqueous sodium hydrogen carbonate and saturated brine
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was evaporated
  5. washthe resulting solid product was washed with diethyl ether
  6. filtrationcollected by filtration

Sources & evidence

ORD record
ord-3e03aa47feeb4a069b4480543ef84765
Source dataset
uspto-grants-2008_09
Patent number
US07429609B2

Linked notes

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