Ethyl Acetate → HCID 86651425, compound

HRID 2403073Notes

Reaction equation

HRID 2403073 reaction equation
[CH:1]1([NH:7][C:8](=[O:28])[CH2:9][C:10]2[CH:15]=[C:14]([I:16])[C:13]([O:17][C:18]3[CH:23]=[C:22]([I:24])[C:21]([OH:25])=[C:20]([I:26])[CH:19]=3)=[C:12]([I:27])[CH:11]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C([O-])([O-])=O.[Cs+].[Cs+].[CH2:35]([CH:37]1[O:39][CH2:38]1)Br.CCOC(C)=O>O1CCOCC1>[CH:1]1([NH:7][C:8](=[O:28])[CH2:9][C:10]2[CH:15]=[C:14]([I:16])[C:13]([O:17][C:18]3[CH:23]=[C:22]([I:24])[C:21]([O:25][CH2:35][CH:37]4[CH2:38][O:39]4)=[C:20]([I:26])[CH:19]=3)=[C:12]([I:27])[CH:11]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 18430EpibromohydrinHCID 67065315HCID 67065315, compound

Product 1

HCID 86651425HCID 86651425, compoundYield 5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Compound 4 (2.0 g, 2.1 mmol, 1.0 eq.) was dissolved in anhydrous dioxane (30 mL), then anhydrous Cs2CO3 (684 mg, 2.1 mmol, 1.0 eq.) was added and then epibromohydrin (1.8 mL, 21.0 mmol, 10.0 eq.) was added dropwise. The reaction medium was then slowly heated to reflux. The mixture was stirred during 12 hours upon reflux then cooled to room temperature. EtOAc (10 mL) was then poured and the precipitate was filtered. EtOH (20 mL) was then added to the solution and the precipitate was filtered off. The remaining solution was analyzed by TLC. The first precipitate was washed thoroughly with EtOAc (30 mL). The organic solution was then evaporated and purified by column chromatography using silica gel (DCM/hexanes 80/20). The product was further recrystallized to give N-cyclohexyl-2-(4-(3,5-diiodo-4-(oxiran-2-ylmethoxy)phenoxy)-3,5-diiodophenyl)acetamide (93 mg, 0.1 mmol) as a powder. The second filtrate and the remaining solution were revealed by TLC to be the starting material which did not react.

Workup

  1. temperatureThe reaction medium was then slowly heated to reflux
  2. temperatureupon reflux
  3. filtrationthe precipitate was filtered
  4. additionEtOH (20 mL) was then added to the solution
  5. filtrationthe precipitate was filtered off
  6. washThe first precipitate was washed thoroughly with EtOAc (30 mL)
  7. customThe organic solution was then evaporated
  8. custompurified by column chromatography
  9. customThe product was further recrystallized

Sources & evidence

ORD record
ord-4ac0515e8bf24367bae6d933f8ad312d
Source dataset
uspto-grants-2014_08
Patent number
US08802240B2

Reaction notes

Loading…