Sodium hydride → HCID 67407442, compound

HRID 1949657Notes

Reaction equation

HRID 1949657 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10](OS(C)(=O)=O)[CH:9]1[CH2:18][CH2:19][NH:20][C:21]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:22])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+]>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH:9]2[CH:10]([N:20]([C:21]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[O:22])[CH2:19][CH2:18]2)[CH2:11][CH2:12]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 76788404HCID 76788404, compound

Product 1

HCID 67407442HCID 67407442, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

A solution containing 113 (2.6 g) in DMF (20 mL) was cooled to 0° C. NaH (60%, 0.28 g, 6.91 mmol) was added in one portion. After 10 min, the reaction mixture was carefully quenched by the addition of saturated aqueous NH4Cl. The mixture was diluted with diethyl ether and water and the layers were separated. The ether layer was washed five times with water to remove DMF then once with brine. The combined aqueous washes were back-extracted with diethyl ether. The combined ether extracts were dried over anhydrous Na2SO4, filtered, and concentrated to afford 1.59 g of crude 114 which was used without further purification. 1H NMR (300 MHz, CDCl3): δ7.36 (m, 5H), 5.15 (m, 2H), 4.35 (m, 2H), 3.77-3.66 (m, 2H), 3.26-3.14 (m, 2H), 2.26 (m, 1H), 2.23 (m, 1H), 1.94 (m, 2H), 1.46 (s, 9H) ppm.

Workup

  1. customthe reaction mixture was carefully quenched by the addition of saturated aqueous NH4Cl
  2. additionThe mixture was diluted with diethyl ether and water
  3. customthe layers were separated
  4. washThe ether layer was washed five times with water
  5. customto remove DMF
  6. extractionThe combined aqueous washes were back-extracted with diethyl ether
  7. dry with materialThe combined ether extracts were dried over anhydrous Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto afford 1.59 g of crude 114 which
  11. customwas used without further purification

Sources & evidence

ORD record
ord-3640c023f06f463ca4df6393677d8b08
Source dataset
uspto-grants-2013_03
Patent number
US08399683B2

Reaction notes

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