Potassium Carbonate → HCID 67173612, compound

HRID 2362239Notes

Reaction equation

HRID 2362239 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:20])[CH2:9][CH2:10][C:11](=[O:19])[CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:4][CH:3]=1.[O:21]1[CH2:25][CH2:24][NH:23][C:22]1=[O:26].N1CCC[C@H]1C(O)=O.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.[Cu]I>[O:19]=[C:11]([CH2:10][CH2:9][C:8](=[O:20])[C:5]1[CH:6]=[CH:7][C:2]([N:23]2[CH2:24][CH2:25][O:21][C:22]2=[O:26])=[CH:3][CH:4]=1)[CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 739492-OxazolidinoneHCID 145742L-ProlineHCID 58297650Ethyl 7-(4-bromophenyl)-4,7-dioxoheptanoate2×

Product 1

HCID 67173612HCID 67173612, compoundYield 10%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 312751,4-DioxaneSolvent

Procedure

To a mixture of ethyl 7-(4-bromophenyl)-4,7-dioxoheptanoate ((36A, where Ar1-Br=4-bromophenyl, also see compound 5B, Scheme 5) (1.50 g, 4.4 mmol) and oxazolidin-2-one (575 mg, 6.6 mmol) in dioxane (5 mL) were added L-proline (50 mg, 0.44 mmol), CuI (42 mg, 0.22 mmol) and K2CO3 (1.22 g, 8.8 mmol). The resultant mixture was stirred under N2 at 110° C. for 48 h and then evaporated. The residue was diluted with EA/water (40 mL/40 mL). The mixture was filtered and the resultant aqueous layer was extracted with EA (30 mL×5). The combined organic layers were washed with brine, dried over NaSO4, concentrated and purified by silica gel column chromatography (pure DCM to DCM:MeOH=30:1) to afford titled compound as a white solid (158 mg, yield 10%).

Workup

  1. customevaporated
  2. additionThe residue was diluted with EA/water (40 mL/40 mL)
  3. filtrationThe mixture was filtered
  4. extractionthe resultant aqueous layer was extracted with EA (30 mL×5)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over NaSO4
  7. concentrationconcentrated
  8. custompurified by silica gel column chromatography (pure DCM to DCM:MeOH=30:1)

Sources & evidence

ORD record
ord-b84fe24db3254451bfba8d9a8475420c
Source dataset
uspto-grants-2014_04
Patent number
US08691816B2

Reaction notes

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