1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 140397795, compound

HRID 1859186Notes

Reaction equation

HRID 1859186 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]([C:11]1[CH:28]=[CH:27][C:14]([O:15][CH2:16][CH2:17][CH2:18][N:19]2[CH2:24][CH2:23][NH:22][C:21](=[O:25])[C:20]2=[O:26])=[CH:13][CH:12]=1)=[NH:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].[N:29]1[CH:34]=[CH:33][CH:32]=[C:31]([CH:35]=[CH:36][C:37]([O:39][CH:40]([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)=[O:38])[CH:30]=1.N12CCCN=C1CCCCC2>CN(C)C=O>[C:1]([O:5][C:6]([NH:8][C:9]([C:11]1[CH:28]=[CH:27][C:14]([O:15][CH2:16][CH2:17][CH2:18][N:19]2[CH2:24][CH2:23][N:22]([CH:35]([C:31]3[CH:30]=[N:29][CH:34]=[CH:33][CH:32]=3)[CH2:36][C:37]([O:39][CH:40]([C:41]3[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=3)[C:47]3[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=3)=[O:38])[C:21](=[O:25])[C:20]2=[O:26])=[CH:13][CH:12]=1)=[NH:10])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 54425842HCID 54425842, compoundHCID 140397783HCID 140397783, compound

Product 1

HCID 140397795HCID 140397795, compoundYield 51.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 7.5 ml of N,N-dimethylformamide was dissolved 2.5 g of 4-[3-(4-tert-butoxycarbonylamidinophenoxy)propyl]-2,3-dioxopiperazine, and to the solution were added 6.1 g of diphenylmethyl 3-(3-pyridyl)acrylate and 0.48 ml of 1,8-diazabicyclo[5.4.0]undec-7-ene. The resulting mixture was stirred overnight at room temperature and distilled under reduced pressure to remove the solvent. To the resulting residue were added 80 ml of ethyl acetate and 60 ml of water and the pH was adjusted to 7 with 2N hydrochloric acid. The organic layer was separated, washed with water and then a saturated aqueous sodium chloride solution, and then distilled under reduced pressure to remove the solvent. The resulting residue was purified by a silica gel column chromatography (eluent; chloroform:methanol 20:1) to obtain 2.34 g of diphenylmethyl 3-[4-[3-(4-tert-butoxycarbonylamidinophenoxy)propyl]-2,3-dioxopiperazin-1-yl]-3-(pyridin-3-yl)propionate as a colorless oil.

Workup

  1. distillationdistilled under reduced pressure
  2. customto remove the solvent
  3. additionTo the resulting residue were added 80 ml of ethyl acetate and 60 ml of water
  4. customThe organic layer was separated
  5. washwashed with water
  6. distillationa saturated aqueous sodium chloride solution, and then distilled under reduced pressure
  7. customto remove the solvent
  8. customThe resulting residue was purified by a silica gel column chromatography (eluent; chloroform:methanol 20:1)

Sources & evidence

ORD record
ord-03efb4e18baa49baaa2feb9640d748d0
Source dataset
uspto-grants-2000_11
Patent number
US06153613

Reaction notes

Loading…