Diethyl Ether → HCID 21201764, compound

HRID 1979293Notes

Reaction equation

HRID 1979293 reaction equation
Br.C(O)(=O)C.Cl.COC[N:10]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[N:14]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:13][CH:12]([NH2:27])[C:11]1=[O:28].CCOCC.Cl[C:35]([O:37][CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)=[O:36]>O1CCCC1.[OH-].[Na+]>[O:28]=[C:11]1[NH:10][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=2[N:14]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:13][CH:12]1[NH:27][C:35]([O:37][CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)=[O:36]

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 10387Benzyl chloroformateHCID 21201625HCID 21201625, compoundHCID 21893785Acetic Acid Mixture with Hydrobromic Acid

Product 1

HCID 21201764HCID 21201764, compoundYield 67.9%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

25% Hydrobromic acid-acetic acid (150 ml) was added to 1-methoxymethyl-2-oxo-3-amino-5-phenyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine hydrochloride (12.2 g). The resultant mixture was stirred for 30 minutes at room temperature. Ether was added thereto, and solid matter so precipitated was collected by filtration, to thereby obtain 2-oxo-3-amino-5-phenyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine hydrobromide. Water (100 ml) was added thereto so as to obtain a suspension. Benzyl chloroformate (6.23 g) in tetrahydrofuran (100 ml) and 1N aqueous sodium hydroxide (75 ml) were added to the suspension under cooling on ice, followed by stirring for one hour at room temperature. The reaction mixture was concentrated under reduced pressure, and water was added thereto, followed by extraction with methylene chloride. The organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1), to thereby obtain 9.6 g of the title compound (yield: 67.9 %).

Workup

  1. customsolid matter so precipitated
  2. filtrationwas collected by filtration
  3. additionWater (100 ml) was added
  4. customso as to obtain a suspension
  5. temperatureunder cooling on ice
  6. concentrationThe reaction mixture was concentrated under reduced pressure, and water
  7. additionwas added
  8. extractionfollowed by extraction with methylene chloride
  9. washThe organic layer was washed with saturated brine
  10. dry with materialdried over anhydrous sodium sulfate
  11. customThe solvent was evaporated under reduced pressure
  12. customThe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-39bef3bc5f8e4c6e8a07ecd194420198
Source dataset
uspto-grants-2001_05
Patent number
US06239131B1

Reaction notes

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