Water → HCID 22243702, compound

HRID 890923Notes

Reaction equation

HRID 890923 reaction equation
[CH3:1][O:2][C:3]1[CH:15]=[CH:14][C:6]([C:7]([NH:9][CH2:10][C:11]([OH:13])=O)=[O:8])=[CH:5][CH:4]=1.C1(N=C=NC2CCCCC2)CCCCC1.[N:31]12[CH2:39][CH2:38][CH:35]([CH2:36][CH2:37]1)[NH:34][CH2:33][CH2:32]2.O>O1CCOCC1>[N:31]12[CH2:39][CH2:38][CH:35]([CH2:36][CH2:37]1)[N:34]([C:11](=[O:13])[CH2:10][NH:9][C:7](=[O:8])[C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:15][CH:14]=1)[CH2:33][CH2:32]2

Participants

6

Reactant 4

HCID 962WaterHCID 10868DicyclohexylcarbodiimideHCID 1288474-Methyoxybenzoyl-N-glycineHCID 3984071,4-Diazabicyclo(3.2.2)nonane

Product 1

HCID 22243702HCID 22243702, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

0.42 g (2 mmol) of N-(4-methoxybenzoyl)glycine dissolved in 20 ml of dioxane is placed in a 50 ml round-bottomed flask, 0.45 g (2.2 mmol) of dicyclohexylcarbodiimide is added, the mixture is stirred at room temperature for 30 minutes, 0.25 g (2 mmol) of 1,4-diazabicyclo[3.2.2]nonane is added and the mixture is stirred for a further one hour. 20 ml of water are added, the precipitate formed is filtered off, the filtrate is extracted with chloroform, the organic phase is extracted with aqueous 0.1N hydrochloric acid solution and the aqueous extraction phase is basified to pH 10 by addition of concentrated aqueous sodium hydroxide solution and extracted with chloroform. The organic phase is dried over sodium sulfate and concentrated under reduced pressure.

Workup

  1. customis placed in a 50 ml round-bottomed flask
  2. stirringthe mixture is stirred for a further one hour
  3. customthe precipitate formed
  4. filtrationis filtered off
  5. extractionthe filtrate is extracted with chloroform
  6. extractionthe organic phase is extracted with aqueous 0.1N hydrochloric acid solution
  7. additionthe aqueous extraction phase is basified to pH 10 by addition of concentrated aqueous sodium hydroxide solution
  8. extractionextracted with chloroform
  9. dry with materialThe organic phase is dried over sodium sulfate
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-beea767faf5d462a9846784031cefb0a
Source dataset
uspto-grants-2006_02
Patent number
US07001902B2

Reaction notes

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