tert-Butyl carbazate → N'-(4-methoxybutyryl)hydrazine carboxylic acid tert-butyl ester

HRID 6924

Reaction equation

HRID 6924 reaction equation
[C:1]([O:5][C:6](=[O:9])[NH:7][NH2:8])([CH3:4])([CH3:3])[CH3:2].[CH3:10][O:11][CH2:12][CH2:13][CH2:14][C:15](O)=[O:16].Cl.C(N=C=NCCCN(C)C)C>N1C=CC=CC=1>[C:1]([O:5][C:6]([NH:7][NH:8][C:15](=[O:16])[CH2:14][CH2:13][CH2:12][O:11][CH3:10])=[O:9])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 70091tert-Butyl carbazateHCID 922644-Methoxybutyric acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 86594808N'-(4-methoxybutyryl)hydrazine carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Carbazic acid tert-butyl ester (9.21 g) was dissolved in pyridine (120 ml), followed by addition of 4-methoxybutyric acid (9.06 g) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride salt (20.0 g), and stirred at ambient temperature for 64 hours. After the reaction solution was concentrated under reduced pressure, ethyl acetate was added to the residue, which was then washed with aqueous 1 mol/liter hydrochloric acid solution, saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium chloride, and dried over anhydrous sodium sulfate. After the solvent was evaporated under reduced pressure, N′-(4-methoxybutyryl)hydrazine carboxylic acid tert-butyl ester was obtained in yellow oil (9.30 g, 57%). The physico-chemical values are as follows.

Workup

  1. concentrationAfter the reaction solution was concentrated under reduced pressure, ethyl acetate
  2. additionwas added to the residue, which
  3. washwas then washed with aqueous 1 mol/liter hydrochloric acid solution, saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. customAfter the solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-23a7463ec365497a8da5e62103007ce0
Source dataset
uspto-grants-2006_08
Patent number
US07084164B2

Linked notes

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