HCID 21201567, compound → HCID 21201602, compound

HRID 1979476Notes

Reaction equation

HRID 1979476 reaction equation
[O:1]=[C:2]1[NH:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[N:5]([CH:13]2[CH2:17][CH2:16][CH:15]=[CH:14]2)[CH2:4][CH:3]1[NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20]>O1CCCC1.[Pt]=O>[O:1]=[C:2]1[NH:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[N:5]([CH:13]2[CH2:14][CH2:15][CH2:16][CH2:17]2)[CH2:4][CH:3]1[NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20]

Participants

4

Reactant 1

HCID 21201567HCID 21201567, compound

Product 1

HCID 21201602HCID 21201602, compoundYield 66.3%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 8028TetrahydrofuranSolvent

Procedure

Platinum oxide (100 mg) was added to a solution of 2-oxo-3-tert-butoxycarbonylamino-5-(2-cyclopenten-1-yl)-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine (1.8 g) in anhydrous tetrahydrofuran (20 ml), the mixture was stirred at room temperature under ambient pressure under hydrogen atmosphere for 2 hours. The reaction mixture was filtrated through a pad of Celite, the filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography(ethyl acetate:n-hexane=1:2). Diisopropyl ether was added to the residue for crystallization, to thereby obtain 1.2 g of the title compound.

Workup

  1. filtrationThe reaction mixture was filtrated through a pad of Celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography(ethyl acetate:n-hexane=1:2)
  4. additionDiisopropyl ether was added to the residue for crystallization

Sources & evidence

ORD record
ord-4a4c2b37eef24263a5049dfcf7b305ae
Source dataset
uspto-grants-2001_05
Patent number
US06239131B1

Reaction notes

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