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1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 22122152, compound

HRID 1859175
Notes
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Reaction equation

HRID 1859175 reaction equation
[N:1]([CH2:4][CH2:5][N:6]1[CH2:11][CH2:10][NH:9][C:8](=[O:12])[C:7]1=[O:13])=[N+:2]=[N-:3].[N:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH:20]=[CH:21][C:22]([O:24][CH:25]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:23])[CH:15]=1.N12CCCN=C1CCCCC2>CN(C)C=O>[N:1]([CH2:4][CH2:5][N:6]1[CH2:11][CH2:10][N:9]([CH:20]([C:16]2[CH:15]=[N:14][CH:19]=[CH:18][CH:17]=2)[CH2:21][C:22]([O:24][CH:25]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)=[O:23])[C:8](=[O:12])[C:7]1=[O:13])=[N+:2]=[N-:3]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 22122160HCID 22122160, compoundHCID 54425842HCID 54425842, compound

Product 1

HCID 22122152HCID 22122152, compoundYield 52.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 0.5 g of 1-(2-azidoethyl)-2,3-dioxopiperazine, 1.72 g of diphenylmethyl 3-(3-pyridyl)-acrylate, 0.2 ml of 1,8-diazabicyclo[5.4.0]undec-7-ene and 2.5 ml of N,N-dimethylformamide was stirred at room temperature for 12 hours. The solvent was distilled off under reduced pressure, after which 30 ml of ethyl acetate and 20 ml of water were added to the resulting residue and the pH was adjusted to 6 with 2N hydrochloric acid. The organic layer was separated and the aqueous layer was extracted with 30 ml of ethyl acetate. The combined organic layer was washed with 20 ml of water and a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the resulting residue was purified by a silica gel column chromatography (eluent; chloroform:methanol=20:1) to obtain 0.71 g of diphenylmethyl 3-[4-(2-azidoethyl)-2,3-dioxopiperazin-1-yl]-3-(pyridin-3-yl)propionate as a light-brown oil.

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. additionafter which 30 ml of ethyl acetate and 20 ml of water were added to the resulting residue
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with 30 ml of ethyl acetate
  5. washThe combined organic layer was washed with 20 ml of water
  6. dry with materiala saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate
  7. distillationThe solvent was distilled off under reduced pressure
  8. customthe resulting residue was purified by a silica gel column chromatography (eluent; chloroform:methanol=20:1)

Sources & evidence

ORD record
ord-58378ebd76e4428ab27293aa489c4e81
Source dataset
uspto-grants-2000_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06153613

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes