Ethyl bromoacetate → 1-ethoxycarbonylmethyl-5-(4-nitrobenzoyl)-1,3,4,5-tetrahydro-1,5-benzodiazepin-2(2H)-one

HRID 441219Notes

Reaction equation

HRID 441219 reaction equation
[H-].[Na+].[N+:3]([C:6]1[CH:25]=[CH:24][C:9]([C:10]([N:12]2[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[NH:16][C:15](=[O:23])[CH2:14][CH2:13]2)=[O:11])=[CH:8][CH:7]=1)([O-:5])=[O:4].Br[CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29]>O1CCCC1>[CH2:31]([O:30][C:28]([CH2:27][N:16]1[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[N:12]([C:10](=[O:11])[C:9]2[CH:8]=[CH:7][C:6]([N+:3]([O-:5])=[O:4])=[CH:25][CH:24]=2)[CH2:13][CH2:14][C:15]1=[O:23])=[O:29])[CH3:32]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 107337945-(4-nitrobenzoyl)-1,3,4,5-tetrahydro-1,5-benzodiazepin-2(2H)-one

Product 1

HCID 106684941-ethoxycarbonylmethyl-5-(4-nitrobenzoyl)-1,3,4,5-tetrahydro-1,5-benzodiazepin-2(2H)-oneYield 67.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a suspension of sodium hydride (60% oil suspension, 154 mg) in tetrahydrofuran (4 ml) was added a solution of 5-(4-nitrobenzoyl)-1,3,4,5-tetrahydro-1,5-benzodiazepin-2(2H)-one (800 mg) in tetrahydrofuran (6 ml) at 0° C. and the mixture was stirred at 0° C. for 5 minutes. To the mixture was added ethyl bromoacetate (472 mg) and then the mixture was stirred at ambient temperature overnight. The reaction was quenched with saturated ammonium chloride aqueous solution and the resultant mixture was diluted with ethyl acetate. The organic layer was washed with saturated sodium bicarbonate aqueous solution and brine, and then it was dried over magnesium sulfate. Filtration and evaporation afforded 1-ethoxycarbonylmethyl-5-(4-nitrobenzoyl)-1,3,4,5-tetrahydro-1,5-benzodiazepin-2(2H)-one (691 mg) as a slightly yellow amorphous.

Workup

  1. stirringthe mixture was stirred at ambient temperature overnight
  2. customThe reaction was quenched with saturated ammonium chloride aqueous solution
  3. additionthe resultant mixture was diluted with ethyl acetate
  4. washThe organic layer was washed with saturated sodium bicarbonate aqueous solution and brine
  5. dry with materialit was dried over magnesium sulfate
  6. filtrationFiltration and evaporation

Sources & evidence

ORD record
ord-b3b82ac9982f427d8298181e78db7d1d
Source dataset
uspto-grants-1996_05
Patent number
US05521170

Reaction notes

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