Sodium hydride → HCID 89498245, compound

HRID 1778921Notes

Reaction equation

HRID 1778921 reaction equation
[CH3:1][C:2]1[N:6]([CH2:7][C:8]2([O:15][CH2:16][CH:17]([OH:20])[CH2:18][OH:19])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)[N:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH:23]([Se](C=C)(=O)=O)=[CH2:24]>ClCCl>[O:20]1[CH2:24][CH2:23][O:19][CH2:18][CH:17]1[CH2:16][O:15][C:8]1([CH2:7][N:6]2[C:2]([CH3:1])=[CH:3][CH:4]=[N:5]2)[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 89501589HCID 89501589, compoundHCID 129756647HCID 129756647, compound

Product 1

HCID 89498245HCID 89498245, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of EXAMPLE 170C (315 mg) in dichloromethane (10 mL) was added NaH (80 mg) at 0° C. The mixture was stirred for 10 minutes. A solution of vinyl selenone (240 mg) in dichloromethane (5 mL) was added to the mixture and the mixture was stirred at room temperature for 3 hours. The mixture was quenched with aqueous NH4Cl, extracted with dichloromethane (2×200 mL), washed with water and brine, and dried over Na2SO4. Filtration and evaporation of the solvent gave the crude product which was purified by column eluted with 50% ethyl acetate in hexane) to provide the title compound.

Workup

  1. stirringthe mixture was stirred at room temperature for 3 hours
  2. customThe mixture was quenched with aqueous NH4Cl
  3. extractionextracted with dichloromethane (2×200 mL)
  4. washwashed with water and brine
  5. dry with materialdried over Na2SO4
  6. filtrationFiltration and evaporation of the solvent
  7. customgave the crude product which
  8. customwas purified by column
  9. washeluted with 50% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-9b6016d05f74452786490ef7b1724d0f
Source dataset
uspto-grants-2016_02
Patent number
US09266877B2

Reaction notes

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