Sodium Chloride → 3-Benzyloxycarbonylamino-1-isobutyl-5-phenyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one

HRID 459897Notes

Reaction equation

HRID 459897 reaction equation
[CH2:1]([O:8][C:9]([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[NH:14][C:13]1=[O:29])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH2:32](I)[CH:33]([CH3:35])[CH3:34].[Cl-].[Na+]>CN(C)C=O.C(Cl)Cl>[CH2:1]([O:8][C:9]([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]([CH2:32][CH:33]([CH3:35])[CH3:34])[C:13]1=[O:29])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 10556Isobutyl iodideHCID 24758Sodium hydrideHCID 2756242Benzyl (2-oxo-5-phenyl-2,3-dihydro-1h-benzo[e][1,4]diazepin-3-yl)carbamate

Product 1

HCID 184442513-Benzyloxycarbonylamino-1-isobutyl-5-phenyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 3-benzyloxycarbonylamino-5-phenyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one (1.00 g, 2.59 mmol) in dimethylformamide (10 mL) was cooled to 0° C. under argon. Sodium hydride (60 wt %, 156 mg, 3.89 mmol) was added followed by isobutyl iodide. Let warm to room temperature and stirred overnight. The reaction was worked up with methylene chloride and saturated sodium chloride. The organic extracts were dried over sodium sulfate, filtered and concentrated. Chromatography (silica gel, 5 to 50% ethyl acetate in hexane gradient elution), giving the title compound (0.92 g). MS 442 (M+1).

Workup

  1. dry with materialThe organic extracts were dried over sodium sulfate
  2. filtrationfiltered
  3. concentrationconcentrated
  4. washChromatography (silica gel, 5 to 50% ethyl acetate in hexane gradient elution)

Sources & evidence

ORD record
ord-bd93299a8c3e41ffbb859196627d6636
Source dataset
uspto-grants-2007_03
Patent number
US07196079B2

Reaction notes

Loading…