Ethyl Acetate → HCID 58005118, compound

HRID 1924363Notes

Reaction equation

HRID 1924363 reaction equation
Br[C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][N:8]=[C:9]2[O:12][C@H:13]2[CH2:17][N:16]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C@H:15]([C:25]([O:27][CH3:28])=[O:26])[CH2:14]2)=[CH:4][CH:3]=1.[CH2:29](C([Sn])=C(CCCC)CCCC)[CH2:30]CC.CCOC(C)=O>C1(C)C=CC=CC=1>[CH:29]([C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][N:8]=[C:9]2[O:12][C@H:13]2[CH2:17][N:16]([C:18]([O:20][C:21]([CH3:22])([CH3:23])[CH3:24])=[O:19])[C@H:15]([C:25]([O:27][CH3:28])=[O:26])[CH2:14]2)=[CH:4][CH:3]=1)=[CH2:30]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 53438229Tri(butyl)vinyltinHCID 58005112HCID 58005112, compound

Product 1

HCID 58005118HCID 58005118, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

Aryl bromide from Step 1 was dissolved in toluene (about 0.15 mM solution) and treated with tributylvinyltin (1.5 eq) and [Ph3P]4Pd(0) (0.05 eq). The reaction mixture was stirred at 100° C. under N2 atmosphere for 2 h. After cooling to RT, the reaction mixture was poured into EtOAc and washed with brine. The organic phase was separated, dried (Na2SO4) and concentrated under reduced pressure. The residue was purified by flash chromatography (SiO2, PE/EtOAc 8/2 v/v as eluent) to give the title compound as a viscous oil. MS (ES+) C22H26N2O5 requires 398. Found: 399 (M+H+).

Workup

  1. temperatureAfter cooling to RT
  2. washwashed with brine
  3. customThe organic phase was separated
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash chromatography (SiO2, PE/EtOAc 8/2 v/v as eluent)

Sources & evidence

ORD record
ord-82f4bf934c4c4050b88eb188fc77e6a2
Source dataset
uspto-grants-2012_05
Patent number
US08178520B2

Reaction notes

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