Sodium hydride → HCID 118093092, compound

HRID 708853Notes

Reaction equation

HRID 708853 reaction equation
[H-].[Na+].[I-].[CH3:4][S+](C)(C)=O.[C:9]([O:13][C:14]([N:16]([CH2:18][C:19]1[CH:24]=[C:23]([NH:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH:22]=[CH:21][C:20]=1[C:33](=[CH2:39])[C:34]([O:36][CH2:37][CH3:38])=[O:35])[CH3:17])=[O:15])([CH3:12])([CH3:11])[CH3:10]>CS(C)=O>[C:9]([O:13][C:14]([N:16]([CH2:18][C:19]1[CH:24]=[C:23]([NH:25][C:26]([O:28][C:29]([CH3:30])([CH3:31])[CH3:32])=[O:27])[CH:22]=[CH:21][C:20]=1[C:33]1([C:34]([O:36][CH2:37][CH3:38])=[O:35])[CH2:4][CH2:39]1)[CH3:17])=[O:15])([CH3:12])([CH3:10])[CH3:11]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 118098727HCID 118098727, compound

Product 1

HCID 118093092HCID 118093092, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

To a suspension of sodium hydride (60% suspension in mineral oil) (0.019 g, 0.473 mmol) in DMSO (2.5 mL), was added trimethylsulfoxonium iodide (0.284 g, 1.291 mmol). The mixture was stirred at rt for 2 h. To the solution was added 15E (0.187 g, 0.430 mmol) in DMSO (2.5 mL) to give a yellow solution. The mixture was stirred at rt for 1 h, quenched with sat. NH4Cl (10 mL), extracted with EtOAc (4×15 mL). Combined organic phase was washed with water (2×10 mL), brine (1×10 mL) and dried (Na2SO4). EtOAc was removed under reduced pressure and the residue was purified by flash chromatography (0-40% EtOAc/hexanes). Fractions were combined and concentrated under reduced pressure to give 15F (0.173 g, 90% yield) as a colorless syrup. MS (ESI) m/z: 449.1 [M+1]+. 1H NMR: (400 MHz, CDCl3) δ ppm 7.34-7.50 (1H, m), 7.20 (1H, d, J=8.08 Hz), 6.83-6.96 (1H, m), 6.44 (1H, br. s.), 4.51 (2H, br. s.), 4.07 (2H, q, J=7.16 Hz), 2.82 (3H, br. s.), 1.35-1.72 (22H, m), 1.15 (3H, t, J=7.07 Hz).

Workup

  1. customto give a yellow solution
  2. stirringThe mixture was stirred at rt for 1 h
  3. customquenched with sat. NH4Cl (10 mL)
  4. extractionextracted with EtOAc (4×15 mL)
  5. washCombined organic phase was washed with water (2×10 mL), brine (1×10 mL)
  6. dry with materialdried (Na2SO4)
  7. customEtOAc was removed under reduced pressure
  8. customthe residue was purified by flash chromatography (0-40% EtOAc/hexanes)
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ddaa78cfe34c4ff18885061a723e7fd1
Source dataset
uspto-grants-2015_11
Patent number
US09174974B2

Reaction notes

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