Ethyl bromoacetate → HCID 18001091, compound

HRID 478372Notes

Reaction equation

HRID 478372 reaction equation
[N+:1]([C:4]1[CH:22]=[CH:21][C:7]([C:8]([N:10]2[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[N:14]=[CH:13][CH:12]=[CH:11]2)=[O:9])=[C:6]([Cl:23])[CH:5]=1)([O-:3])=[O:2].Br[CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27].C1CCN2C(=NCCC2)CC1>C(#N)C>[N+:1]([C:4]1[CH:22]=[CH:21][C:7]([C:8]([N:10]2[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[N:14]([CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH2:13][CH2:12][CH2:11]2)=[O:9])=[C:6]([Cl:23])[CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 18001068HCID 18001068, compound

Product 1

HCID 18001091HCID 18001091, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-[4-Nitro-2-chlorobenzoyl]-1,5-benzodiazepine (5 g) and ethyl bromoacetate (16.7 ml) are dissolved in acetonitrile (100 ml), and thereto is added dropwise 1,8-diazabicyclo[5.4.0]-7-undecene (11.3 ml). The mixture is refluxed for two days, concentrated, and thereto are added water and chloroform, and extracted. The extract is dried over sodium carbonate, and purified by silica gel column chromatography (solvent; n-hexane:ethyl acetate=4:1→1:1) to give 1-(4-nitro-2-chlorobenzoyl)-5-ethoxycarbonylmethyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine (4.4 g) as pale yellow oil.

Workup

  1. temperatureThe mixture is refluxed for two days
  2. concentrationconcentrated
  3. additionare added water and chloroform
  4. extractionextracted
  5. dry with materialThe extract is dried over sodium carbonate
  6. custompurified by silica gel column chromatography (solvent; n-hexane:ethyl acetate=4:1→1:1)

Sources & evidence

ORD record
ord-72507d7f12c7426eab8b32c952064407
Source dataset
uspto-grants-2003_11
Patent number
US06642223B2

Reaction notes

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