Water → Benzyl (2-oxo-5-phenyl-2,3-dihydro-1h-benzo[e][1,4]diazepin-3-yl)carbamate

HRID 1290702

Reaction equation

HRID 1290702 reaction equation
[C:1]([NH:11][CH:12]1[N:18]=[C:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:16]2[CH:25]=[CH:26][CH:27]=[CH:28][C:15]=2[N:14](CC2C=CC(OC)=CC=2)[C:13]1=[O:38])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].O.[N+]([O-])([O-])=O.[Ce+4].[NH4+].[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.C(C(C(C([O-])=O)O)O)([O-])=O.[K+].[Na+]>C(#N)C.C(OCC)(=O)C>[C:1]([NH:11][CH:12]1[N:18]=[C:17]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:16]2[CH:25]=[CH:26][CH:27]=[CH:28][C:15]=2[NH:14][C:13]1=[O:38])([O:3][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)=[O:2]

Participants

7

Reactant 4

HCID 962Water2×HCID 9855836Potassium sodium tartarateHCID 9869224Ammonium cerium (IV) nitrateHCID 18917688(+/-) 3-[N-carbobenzyloxy]amino-2,3-dihydro-1-[4-methoxybenzyl]-2-oxo-5-phenyl-1H-1,4-benzodiazepine

Product 1

HCID 2756242Benzyl (2-oxo-5-phenyl-2,3-dihydro-1h-benzo[e][1,4]diazepin-3-yl)carbamate

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of (±) 3-[N-carbobenzyloxy]amino-2,3-dihydro-1-[4-methoxybenzyl]-2-oxo-5-phenyl-1H-1,4-benzodiazepine (0.58 g, 1.15 mmol, from step 5 of Example 1) in a mixture of acetonitrile (3.3 mL), water (1.2 mL) and ammonium cerium(IV) nitrate (3.1 g) was vortexed vigorously for 5 minutes. The resultant clear orange solution was stirred at room temperature for 20 minutes and add dropwisely into a mixture of saturated sodium potassium tartrate solution (40 mL), water (27 mL), and ethyl acetate (190 mL). The resultant mixture was stirred at room temperature for 1.5 hour, and the organic extract was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated under vacuo. The residue was subjected to column chromatography on silica gel eluting with 2% methanol in chloroform. Collection and concentration of appropriate fraction provided the title compound.

Workup

  1. extractionthe organic extract
  2. washwas washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under vacuo
  6. customCollection and concentration of appropriate fraction

Sources & evidence

ORD record
ord-dc64e52ecc43483fa1c80890a2726cb6
Source dataset
uspto-grants-1998_05
Patent number
US05753650

Linked notes

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