1,4-Dioxane hydrochloride → HCID 21201603, compound

HRID 1979300Notes

Reaction equation

HRID 1979300 reaction equation
Cl.O1[CH2:7][CH2:6]OCC1.[C:8]1([CH3:49])[C:9]([C:14]([CH2:16][N:17]2[C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=3[N:21]([C:28]([C:30]34[CH2:39][CH:34]5[CH2:35][CH:36]([CH2:38][CH:32]([CH2:33]5)[CH2:31]3)[CH2:37]4)=[O:29])[CH2:20][CH:19]([NH:40][C:41](OC(C)(C)C)=[O:42])[C:18]2=[O:48])=[O:15])=[CH:10][CH:11]=[CH:12][CH:13]=1>C(O)C>[C:8]1([CH3:49])[C:9]([C:14]([CH2:16][N:17]2[C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=3[N:21]([C:28]([C:30]34[CH2:37][CH:36]5[CH2:35][CH:34]([CH2:33][CH:32]([CH2:38]5)[CH2:31]3)[CH2:39]4)=[O:29])[CH2:20][CH:19]([NH:40][C:41]([NH:17][C:23]3[CH:22]=[CH:27][CH:26]=[C:6]([CH3:7])[CH:24]=3)=[O:42])[C:18]2=[O:48])=[O:15])=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 21201702HCID 21201702, compound

Product 1

HCID 21201603HCID 21201603, compoundYield 93.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

4N HCl-dioxane (5.0 ml) was added to 1-(2-toluoylmethyl)-2-oxo-3-tert-butoxycarbonylamino-5-(adamantan-1-yl)carbonyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine (400 mg) in anhydrous ethanol (15 ml), and the mixture was stirred at 50° C. for 15 minutes. The reaction mixture was concentrated under reduced pressure, and saturated aqueous sodium bicarbonate was added to the residue, followed by extraction with methylene chloride. The organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure, to thereby obtain 1-(2-toluoylmethyl)-2-oxo-3-amino-5-(adamantan-1-yl)carbonyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine. Subsequently, this compound was dissolved in anhydrous tetrahydrofuran (10 ml), and m-tolyl isocyanate (0.10 ml) was added to thereto. The mixture was stirred at room temperature for 15 minutes. The solvent was evaporated under reduced pressure. A solvent mixture of isopropyl ether and ethanol was added thereto for solidification and collection by filtration, to thereby obtain 394 mg of the title compound (yield: 93.1%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, and saturated aqueous sodium bicarbonate
  2. additionwas added to the residue
  3. extractionfollowed by extraction with methylene chloride
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. dissolutionSubsequently, this compound was dissolved in anhydrous tetrahydrofuran (10 ml)
  7. additionm-tolyl isocyanate (0.10 ml) was added to thereto
  8. stirringThe mixture was stirred at room temperature for 15 minutes
  9. customThe solvent was evaporated under reduced pressure
  10. additionA solvent mixture of isopropyl ether and ethanol
  11. additionwas added
  12. customfor solidification and collection
  13. filtrationby filtration

Sources & evidence

ORD record
ord-54cd828cab6341d6beab4c4409c6a4c1
Source dataset
uspto-grants-2001_05
Patent number
US06239131B1

Reaction notes

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