Acetohydrazide → tert-Butyl (2-(2-acetylhydrazinyl)-2-oxoethyl)carbamate

HRID 1894713Notes

Reaction equation

HRID 1894713 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCOC1N(C(OCC)=O)C2C(=CC=CC=2)C=C1.[C:31]([NH:34][NH2:35])(=[O:33])[CH3:32]>ClCCl>[C:1]([O:5][C:6](=[O:7])[NH:8][CH2:9][C:10]([NH:35][NH:34][C:31](=[O:33])[CH3:32])=[O:12])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 14039AcetohydrazideHCID 278332-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinolineHCID 78288N-(tert-butoxycarbonyl)glycine

Product 1

HCID 59892150tert-Butyl (2-(2-acetylhydrazinyl)-2-oxoethyl)carbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under N2 atmosphere, to a dichloromethane 10 mL solution of N-tert-butyloxycarbonyl-glycine (500 mg, 2.85 mmol) was added EEDQ (706 mg, 2.85 mmol). After stirring for 15 min, to it was added acethydrazide (260 mg, 3.51 mmol) and stirring continued at rt overnight. The precipitate was collected by suction filtration to give the title compound as white fluffy solid (496 mg).

Workup

  1. stirringstirring
  2. waitcontinued at rt overnight
  3. filtrationThe precipitate was collected by suction filtration

Sources & evidence

ORD record
ord-30927353c6a44b069755079871ad1105
Source dataset
uspto-grants-2013_08
Patent number
US08513289B2

Reaction notes

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