Sodium hydride → HCID 46928226, compound

HRID 2036279Notes

Reaction equation

HRID 2036279 reaction equation
[CH2:1]([O:3][C:4](=[O:24])[CH:5]([C:11]1[S:12][N:13]=[C:14]2[C:19]=1[C:18](=[O:20])[N:17]([CH3:21])[C:16](=[O:22])[N:15]2[CH3:23])C(OCC)=O)[CH3:2].[H-].[Na+]>C(O)C>[CH2:1]([O:3][C:4](=[O:24])[CH2:5][C:11]1[S:12][N:13]=[C:14]2[C:19]=1[C:18](=[O:20])[N:17]([CH3:21])[C:16](=[O:22])[N:15]2[CH3:23])[CH3:2]

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 66697524HCID 66697524, compound

Product 1

HCID 46928226HCID 46928226, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of Step 4 intermediate (13.8 g, 38.8 mmol) in dry ethanol (155 ml) was added a catalytic amount of sodium hydride (60% dispersion in mineral oil, 355 mg, 8.87 mmol) at room temperature and the reaction mixture was refluxed for 48 h under nitrogen atmosphere. Excess of solvent was removed under reduced pressure and the residue was cooled in ice bath, 1 N HCl was added slowly to the reaction mixture, solid obtained was collected by filtration and dried to give 9.1 g of the product as a yellow solid; 1H NMR (300 MHz, DMSO-d6) δ 1.34 (t, J=6.9 Hz, 3H), 3.40 (s, 3H), 3.63 (s, 3H), 4.30 (q, J=6.9 Hz, 2H), 4.50 (s, 2H)

Workup

  1. temperaturethe reaction mixture was refluxed for 48 h under nitrogen atmosphere
  2. customExcess of solvent was removed under reduced pressure
  3. temperaturethe residue was cooled in ice bath
  4. addition1 N HCl was added slowly to the reaction mixture, solid
  5. customobtained
  6. filtrationwas collected by filtration
  7. customdried

Sources & evidence

ORD record
ord-32b748376652406e8840bbba559ec938
Source dataset
uspto-grants-2013_11
Patent number
US08575178B2

Reaction notes

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