Water → HCID 22243705, compound

HRID 890924Notes

Reaction equation

HRID 890924 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][CH:14]=1)[C:5]([NH:7][CH2:8][C:9]([OH:11])=O)=[O:6].C1(N=C=NC2CCCCC2)CCCCC1.[N:30]12[CH2:38][CH2:37][CH:34]([CH2:35][CH2:36]1)[NH:33][CH2:32][CH2:31]2.O>O1CCOCC1>[N:30]12[CH2:38][CH2:37][CH:34]([CH2:35][CH2:36]1)[N:33]([C:9](=[O:11])[CH2:8][NH:7][C:5](=[O:6])[C:4]1[CH:12]=[CH:13][CH:14]=[C:2]([Br:1])[CH:3]=1)[CH2:32][CH2:31]2

Participants

6

Reactant 4

HCID 962WaterHCID 10868DicyclohexylcarbodiimideHCID 3984071,4-Diazabicyclo(3.2.2)nonaneHCID 787887HCID 787887, compound

Product 1

HCID 22243705HCID 22243705, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

0.77 g (3 mmol) of N-(3-bromobenzoyl)glycine dissolved in 30 ml of dioxane is placed in a 100 ml round-bottomed flask, 0.68 g (3.3 mmol) of dicyclohexylcarbodiimide is added and the mixture is stirred at room temperature for 30 minutes, 0.38 g (3 mmol) of 1,4-diazabicyclo[3.2.2]nonane is added and the mixture is stirred for a further two hours. 30 ml of water are added and the precipitate formed is filtered off, the filtrate is extracted with chloroform and the organic phase is then extracted with aqueous 0.1N hydrochloric acid solution. 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 100 ml round-bottomed flask
  2. stirringthe mixture is stirred for a further two hours
  3. customthe precipitate formed
  4. filtrationis filtered off
  5. extractionthe filtrate is extracted with chloroform
  6. extractionthe organic phase is then 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-f2d88539f56744cf878648270df29abd
Source dataset
uspto-grants-2006_02
Patent number
US07001902B2

Reaction notes

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