Sodium Carbonate → methyl 5-(N-hydroxycarbamimidoyl)pentanoate

HRID 1039186Notes

Reaction equation

HRID 1039186 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].[CH3:7][O:8][C:9](=[O:16])[CH2:10][CH2:11][CH2:12][CH2:13][C:14]#[N:15].Cl.[NH2:18][OH:19]>C(O)C>[OH:19][NH:18][C:14]([CH2:13][CH2:12][CH2:11][CH2:10][C:9]([O:8][CH3:7])=[O:16])=[NH:15]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 554130Methyl 5-cyanopentanoate

Product 1

HCID 178500328methyl 5-(N-hydroxycarbamimidoyl)pentanoateYield 87%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Add sodium carbonate (4.5 g, 42 mmol) to a solution of commercially available 5-cyano-pentanoic acid methyl ester (5.0 g, 35 mmol) and hydroxylamine hydrochloride (2.9 g, 42 mmol) in ethanol (100 mL) at room temperature under nitrogen and heat the mixture at reflux for 5.5 h. Filter the mixture through celite and remove the solvent under reduced pressure to provide crude methyl 5-(N-hydroxycarbamimidoyl)pentanoate (5.3 g, 87% yield), which is carried forward without further purification.

Workup

  1. temperatureheat the mixture
  2. temperatureat reflux for 5.5 h
  3. filtrationFilter the mixture through celite
  4. customremove the solvent under reduced pressure

Sources & evidence

ORD record
ord-7e662e83efbc49e9b4a38efd8381f4ea
Source dataset
uspto-grants-2013_10
Patent number
US08552039B2

Reaction notes

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