3-(Nalpha-carbobenzoxyglycyl-glycylamino)-4-hydroxy-4-phenyl-6-chloro-3,4-dihydroquinazoline → 5-chloro-2-[3-(N-carbobenzoxyglycyl)aminomethyl-4H-1,2,4-triazol-4-yl]-benzophenone

HRID 1391289Notes

Reaction equation

HRID 1391289 reaction equation
[C:1]([NH:11][CH2:12][C:13]([NH:15][CH2:16][C:17]([NH:19][N:20]1[C:29]([OH:36])([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:28]2[C:23](=[CH:24][CH:25]=[C:26]([Cl:37])[CH:27]=2)[N:22]=[CH:21]1)=O)=[O:14])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2]>C(O)(=O)C>[Cl:37][C:26]1[CH:25]=[CH:24][C:23]([N:22]2[CH:21]=[N:20][N:19]=[C:17]2[CH2:16][NH:15][C:13](=[O:14])[CH2:12][NH:11][C:1]([O:3][CH2:4][C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)=[O:2])=[C:28]([CH:27]=1)[C:29]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:36]

Participants

3

Reactant 1

HCID 155678413-(Nalpha-carbobenzoxyglycyl-glycylamino)-4-hydroxy-4-phenyl-6-chloro-3,4-dihydroquinazoline

Product 1

HCID 213256755-chloro-2-[3-(N-carbobenzoxyglycyl)aminomethyl-4H-1,2,4-triazol-4-yl]-benzophenoneYield 35.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 3-(Nα -carbobenzoxyglycyl-glycylamino)-4-hydroxy-4-phenyl-6-chloro-3,4-dihydroquinazoline (1.5 g) in acetic acid (20 ml) is refluxed with heating for 2 hours. The reaction mixture is evaporated under reduced pressure, and the residue is dissolved in ethyl acetate (30 ml). The ethyl acetate layer is washed with aqueous sodium bicarbonate and water in order, dried over sodium sulfate and evaporated under reduced pressure to remove the solvent. The residue is chromatographed on a column of silica gel, which is eluted with ethyl acetate/methanol to give 5-chloro-2-[3-(N-carbobenzoxyglycyl)aminomethyl-4H-1,2,4-triazol-4-yl]-benzophenone as a colorless oil (0.515 g).

Workup

  1. temperaturewith heating for 2 hours
  2. customThe reaction mixture is evaporated under reduced pressure
  3. dissolutionthe residue is dissolved in ethyl acetate (30 ml)
  4. washThe ethyl acetate layer is washed with aqueous sodium bicarbonate and water in order
  5. dry with materialdried over sodium sulfate
  6. customevaporated under reduced pressure
  7. customto remove the solvent
  8. customThe residue is chromatographed on a column of silica gel, which
  9. washis eluted with ethyl acetate/methanol

Sources & evidence

ORD record
ord-da78285623784051991522da092eabd7
Source dataset
uspto-grants-1979_02
Patent number
US04141901

Reaction notes

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