Ethyl 2-bromopropionate → HCID 13909862, compound

HRID 973891Notes

Reaction equation

HRID 973891 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[C:9]2[N:17]3[N:12]([CH2:13][CH2:14][CH2:15][CH2:16]3)[C:11](=[O:18])[S:10]2)=[CH:4][C:3]=1[NH2:19].Br[CH:21]([CH3:27])[C:22]([O:24][CH2:25][CH3:26])=[O:23].C(=O)([O-])O.[Na+]>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[C:9]2[N:17]3[N:12]([CH2:13][CH2:14][CH2:15][CH2:16]3)[C:11](=[O:18])[S:10]2)=[CH:4][C:3]=1[NH:19][CH:21]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH3:27]

Participants

4

Reactant 3

HCID 79040Ethyl 2-bromopropionateHCID 516892Sodium BicarbonateHCID 19987017HCID 19987017, compound

Product 1

HCID 13909862HCID 13909862, compoundYield 52%

Procedure

Into a reaction flask equipped with a Dimroth condenser, 2.2 g (7.4 mmol) of 9-(4-chloro-3-aminophenylimino)-8-thia-1,6-diazabicyclo[4.3.0]nonane-7-one, 15 ml of ethyl 2-bromopropionate and 2.0 g (24 mmol) of sodium hydrogen carbonate, were charged, and refluxed under heating for 4 hours to complete the reaction. The reaction solution was filtered, concentrated and extracted with ethyl acetate, and then washed with water and dried over anhydrous sodium sulfate. The solvent was distilled off to obtain a crude product, which was purified by column chromatography to obtain 1.5 g (yield: 52%) of colorless oily substance. Refractive index: nD20 1.5755

Workup

  1. additionwere charged
  2. temperaturerefluxed
  3. temperatureunder heating for 4 hours
  4. customthe reaction
  5. filtrationThe reaction solution was filtered
  6. concentrationconcentrated
  7. extractionextracted with ethyl acetate
  8. washwashed with water
  9. dry with materialdried over anhydrous sodium sulfate
  10. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-edfb09f749ad4b5996f1df87e189e648
Source dataset
uspto-grants-1991_11
Patent number
USRE033745

Reaction notes

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