Sodium hydride → HCID 22049424, compound

HRID 2087153Notes

Reaction equation

HRID 2087153 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:5]=[C:6]([CH:11]2[C:15]([CH3:17])([CH3:16])[O:14][C:13](=[O:18])[NH:12]2)[CH:7]=[CH:8][C:9]=1[F:10].Cl[C:20]([O:22][C:23]1[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][CH:24]=1)=[O:21]>C1COCC1>[F:3][C:4]1[CH:5]=[C:6]([CH:11]2[C:15]([CH3:16])([CH3:17])[O:14][C:13](=[O:18])[N:12]2[C:20]([O:22][C:23]2[CH:24]=[CH:25][C:26]([N+:29]([O-:31])=[O:30])=[CH:27][CH:28]=2)=[O:21])[CH:7]=[CH:8][C:9]=1[F:10]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 821294-Nitrophenyl chloroformateHCID 22049200HCID 22049200, compound

Product 1

HCID 22049424HCID 22049424, compoundYield 60.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

Into a stirred suspension of sodium hydride (60% suspension in paraffin 203 mg, 1.4 eq.) in THF (20 mL) at 0° C., a solution of 4-(3,4-difluorophenyl)-5,5-dimethyl-2-oxo-oxazolidine (870 mg, 3.622 mmol) in THF (5 mL) was added followed by stirring for 30 minutes. This suspension was added to a solution of 4-nitrophenyl chloroformate (950 mg, 4.71 mmol) in THF (20 mL) at −78° C. under argon and the stirring was continued for 2 h. It was slowly warmed to room temperature and after 4 h the solvent was evaporated. The residue was mixed with dichloromethane (150 mL), washed with 0.05 N sodium hydroxide (3×10 mL), and dried (sodium sulfate). The solvent was evaporated and the residue was purified by column chromatography on silica gel using chloroform/ethyl acetate (9:1) as the eluent to give the product as a white powder (860 mg, 59% yield).

Workup

  1. waitthe stirring was continued for 2 h
  2. customwas evaporated
  3. additionThe residue was mixed with dichloromethane (150 mL)
  4. washwashed with 0.05 N sodium hydroxide (3×10 mL)
  5. dry with materialdried (sodium sulfate)
  6. customThe solvent was evaporated
  7. customthe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-b1ef4df11cee4e1e96cc20a654bb95f3
Source dataset
uspto-grants-2004_04
Patent number
US06727264B1

Reaction notes

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