Isobutylamine → (E)-N-isobutyl-diethylphosphonocrotonic acid amide

HRID 333042Notes

Reaction equation

HRID 333042 reaction equation
[CH2:1]([O:3][P:4]([CH2:9]/[CH:10]=[CH:11]/C(O)=O)([O:6][CH2:7][CH3:8])=[O:5])[CH3:2].Cl.C(N=C=NCCCN(C)C)C.[OH:27][C:28]1C2N=NNC=2C=CC=1.[CH2:37]([NH2:41])[CH:38]([CH3:40])[CH3:39].C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[CH2:37]([NH:41][C:28](=[O:27])/[C:9](/[P:4]([O:3][CH2:1][CH3:2])([O:6][CH2:7][CH3:8])=[O:5])=[CH:10]\[CH3:11])[CH:38]([CH3:40])[CH3:39]

Participants

7

Reactant 5

HCID 6558IsobutylamineHCID 10340Sodium CarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 6285301(E)-4-(Diethoxyphosphoryl)but-2-enoic acidHCID 178418300HCID 178418300, compound

Product 1

HCID 86698216(E)-N-isobutyl-diethylphosphonocrotonic acid amide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-diethylphosphonocrotonic acid (5.0 g), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (5.2 g) and HO-Bt (hydroxybenzotriazole) (4.6 g) in dichloromethane (36.5 g) was stirred for 5 minutes under argon atmosphere. To the above reaction solution was added isobutylamine (4.9 mL), and the reaction solution was stirred at room temperature for 6 hours. A saturated sodium carbonate aqueous solution was added to the resulting reaction solution, and the water layer was extracted with dichloromethane. The combined organic layer was dried over anhydrous sodium sulfate. The organic solvent was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (ethyl acetat→ethyl acetate/methanol=10/1) to give (E)-N-isobutyl-diethylphosphonocrotonic acid amide as colorless viscous oil.

Workup

  1. extractionthe water layer was extracted with dichloromethane
  2. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate
  3. concentrationThe organic solvent was concentrated under reduced pressure
  4. customthe residue was purified by silica gel chromatography (ethyl acetat→ethyl acetate/methanol=10/1)

Sources & evidence

ORD record
ord-35a3bd2771f648669ba905f318dc4934
Source dataset
uspto-grants-2014_11
Patent number
US08877953B2

Reaction notes

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