Pyridine → HCID 66725717, compound

HRID 393344Notes

Reaction equation

HRID 393344 reaction equation
N[CH:2]1[CH2:6][N:5](C(CC)C(N)=[O:9])[C:4](=[O:13])[CH2:3]1.CO[C:16]1([O:21][CH3:22])[CH2:20][CH2:19][CH2:18]O1.N1C=CC=CC=1>CC(O)=O>[NH:5]1[CH2:6][CH2:2][CH2:3][C:4]1=[O:13].[O:21]1[CH:22]=[CH:18][C:19]([OH:9])=[CH:20][CH2:16]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 11788317dimethoxytetrahydrofuraneHCID 22386994HCID 22386994, compound

Product 1

HCID 66725717HCID 66725717, compoundYield 39.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
70 °C

Procedure

In a three necked flask, under argon, a suspension of 2-[4-amino-2-oxo-1-pyrrolidinyl]butanamide 393 (6.99 g, 0.037 mol.), dimethoxytetrahydrofurane (5.53 g, 0.041 mol.), pyridine (50.6 ml) and AcOH (36 ml) is warmed to 70° C. and dissolution occurs. After 2 h at this temperature, the reaction is cooled down to room temperature, concentrated in vacuo and the crude product is purified by chromatography on silicagel (CH2Cl2/MeOH: 95/05 (v/v)) to afford 223 as an oil (2.67 g, 30.1%).

Workup

  1. dissolutiondissolution
  2. temperaturethe reaction is cooled down to room temperature
  3. concentrationconcentrated in vacuo
  4. customthe crude product is purified by chromatography on silicagel (CH2Cl2/MeOH: 95/05 (v/v))

Sources & evidence

ORD record
ord-6115764402b54b248225ad88916620f3
Source dataset
uspto-grants-2004_10
Patent number
US06806287B2

Reaction notes

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