Triethylamine → 1-(1-tert-butylcarbonylmethyl-2-oxo-5-phenyl-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl)-3-(3-ethoxycarbonylphenyl)urea

HRID 1979367Notes

Reaction equation

HRID 1979367 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6].Cl[C:14](Cl)([O:16]C(=O)OC(Cl)(Cl)Cl)Cl.C(N(CC)CC)C.[C:32]([C:36]([CH2:38][N:39]1[C:45]2[CH:46]=[C:47]([CH3:50])[CH:48]=[CH:49][C:44]=2[N:43]([C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)[CH2:42][CH:41]([NH2:57])[C:40]1=[O:58])=[O:37])([CH3:35])([CH3:34])[CH3:33]>O1CCCC1>[C:32]([C:36]([CH2:38][N:39]1[C:45]2[CH:46]=[C:47]([CH3:50])[CH:48]=[CH:49][C:44]=2[N:43]([C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)[CH2:42][CH:41]([NH:57][C:14]([NH:1][C:2]2[CH:12]=[CH:11][CH:10]=[C:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH:3]=2)=[O:16])[C:40]1=[O:58])=[O:37])([CH3:35])([CH3:33])[CH3:34]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 11400Ethyl 3-aminobenzoateHCID 94429TriphosgeneHCID 212019411-tert-butylcarbonylmethyl-2-oxo-3-amino-5-phenyl-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine

Product 1

HCID 212016521-(1-tert-butylcarbonylmethyl-2-oxo-5-phenyl-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl)-3-(3-ethoxycarbonylphenyl)ureaYield 593.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Ethyl 3-aminobenzoate (14 mg) was dissolved in anhydrous tetrahydrofuran (10 ml), under ice-cooling triphosgene (68 mg) was added and triethylamine (60 μl ) was added thereto five times. The mixture was stirred for 30 minutes at same temperature. A solution of 1-tert-butylcarbonylmethyl-2-oxo-3-amino-5-phenyl-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine (227 mg) in anhydrous tetrahydrofuran (10 ml) was added, the resultant mixture was allowed to come to room temperature, and stirred for 30 minutes. The reaction mixture was concentrated under reduced pressure, Water (50 ml) was added, and extracted with methylene chloride. The organic layer was dried over anhydrous sodium sulfate, the solvent was evaporated under reduced pressure, and diethyl ether was added to the residue for trituration, collected by filtration, to thereby obtain 280 mg of the titled compound (Yield: 81.1%).

Workup

  1. additionwas added
  2. customto come to room temperature
  3. stirringstirred for 30 minutes
  4. concentrationThe reaction mixture was concentrated under reduced pressure, Water (50 ml)
  5. additionwas added
  6. extractionextracted with methylene chloride
  7. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  8. customthe solvent was evaporated under reduced pressure, and diethyl ether
  9. additionwas added to the residue for trituration
  10. filtrationcollected by filtration

Sources & evidence

ORD record
ord-1ddc6a56957e44d1a87332eaf268660e
Source dataset
uspto-grants-2001_05
Patent number
US06239131B1

Reaction notes

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