Hydrochloric Acid → HCID 10526954, compound

HRID 1596364Notes

Reaction equation

HRID 1596364 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH:12]1[N:18]=[C:17]([CH2:19][CH3:20])[C:16]2[CH:21]=[CH:22][CH:23]=[C:24]([CH3:25])[C:15]=2[NH:14][C:13]1=[O:26])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32].Cl>CN(C)C=O>[CH2:1]([O:8][C:9]([NH:11][CH:12]1[N:18]=[C:17]([CH2:19][CH3:20])[C:16]2[CH:21]=[CH:22][CH:23]=[C:24]([CH3:25])[C:15]=2[N:14]([CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])[C:13]1=[O:26])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 135503838HCID 135503838, compound

Product 1

HCID 10526954HCID 10526954, compoundYield 124.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of (3RS)-3-benzyloxycarbonylamino-5-ethyl-2,3-dihydro-9-methyl-1H-1,4-benzodiazepin-2-one (1.0 g) and 60% sodium hydride (120 mg) in N,N-dimethylformamide was stirred at 0° C. for 1 hour and at room temperature for 3 hours. To the resultant mixture was added dropwise ethyl bromoacetate (476 mg) under cooling at 0-5° C. in an ice-bath. The mixture was stirred for 5.5 hours under the same conditions. The reaction mixture was poured into 0.1N aqueous hydrochloric acid and extracted with ethyl acetate. The extract was washed with water twice, saturated aqueous sodium bicarbonate and brine successively and dried over magnesium sulfate. The solvent was evaporated in vacuo to afford (3RS)-3-benzyloxycarbonylamino-5-ethyl-2,3-dihydro-1-ethoxycarbonylmethyl-9-methyl-1H-1,4-benzodiazepin-2-one (1.55 g) as an oil.

Workup

  1. temperatureunder cooling at 0-5° C. in an ice-bath
  2. stirringThe mixture was stirred for 5.5 hours under the same conditions
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with water twice
  5. dry with materialsaturated aqueous sodium bicarbonate and brine successively and dried over magnesium sulfate
  6. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-96f5417615fc40518897e907687a3647
Source dataset
uspto-grants-2001_09
Patent number
US06291452B1

Reaction notes

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