3-Iodobenzyl bromide → HCID 89559790, compound

HRID 1747225Notes

Reaction equation

HRID 1747225 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5]Br.CC(C)(C)C=[N:13][CH:14]([CH3:20])[C:15]([O:17][CH2:18][CH3:19])=[O:16].CC([O-])(C)C.[K+]>C1(C)C=CC=CC=1>[CH2:18]([O:17][C:15](=[O:16])[C:14]([NH2:13])([CH3:20])[CH2:5][C:4]1[CH:7]=[CH:8][CH:9]=[C:2]([I:1])[CH:3]=1)[CH3:19]

Participants

5

Reactant 3

HCID 27593613-Iodobenzyl bromideHCID 10797610HCID 10797610, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 89559790HCID 89559790, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

3-Iodobenzyl bromide (14.4 g, 48.6 mmol) was added to a RT solution of rac-ethyl 2-((2,2-dimethylpropylidene)amino)propanoate (10 g, 48.6 mmol) from above in toluene (100 mL) under argon and the resulting mixture was cooled to −10° C. before KOtBu (10.9 g, 97.2 mmol) was added portionwise. The reaction mixture was stirred at 0° C. for 4 h before being quenched with water. The toluene was evaporated in vacuo and the remaining aqueous phase was extracted with EtOAC (3×). The combined organic extracts were dried over Na2SO4, filtered and evaporated in vacuo. The residue was stirred in 1M aq. HCl overnight after which LCMS showed the desired product. EtOAc was added and the mixture was stirred for 30 min before the layers were separated. The organic phase was discarded and the aqueous phase was basified with 2M aq. NaOH and re-extracted with EtOAc (3×). The combined organic extracts were dried over Na2SO4, filtered and evaporated in vacuo to give the title compound that was used further without purification. LC-MS D: tR=0.88 min; [M+H+MeCN]+=375.06.

Workup

  1. additionwas added portionwise
  2. custombefore being quenched with water
  3. customThe toluene was evaporated in vacuo
  4. extractionthe remaining aqueous phase was extracted with EtOAC (3×)
  5. dry with materialThe combined organic extracts were dried over Na2SO4
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. stirringThe residue was stirred in 1M aq. HCl overnight after which LCMS
  9. additionEtOAc was added
  10. stirringthe mixture was stirred for 30 min before the layers
  11. customwere separated
  12. extractionre-extracted with EtOAc (3×)
  13. dry with materialThe combined organic extracts were dried over Na2SO4
  14. filtrationfiltered
  15. customevaporated in vacuo

Sources & evidence

ORD record
ord-6be5f17922264fd7ab6a24b603f25d20
Source dataset
uspto-grants-2015_10
Patent number
US09150566B2

Reaction notes

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