Sodium hydride → (R)-4-benzyl-3-[2-(3-fluoro-4-methoxy-phenyl)-cyclopropanecarbonyl]-oxazolidin-2-on

HRID 62909Notes

Reaction equation

HRID 62909 reaction equation
[CH2:1]([C@@H:8]1[CH2:12][O:11][C:10](=[O:13])[NH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[F:16][C:17]1[CH:18]=[C:19]([CH:25]2[CH2:27][CH:26]2[C:28](Cl)=[O:29])[CH:20]=[CH:21][C:22]=1[O:23][CH3:24].[NH4+].[Cl-]>C1COCC1>[CH2:1]([C@@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:28]([CH:26]1[CH2:27][CH:25]1[C:19]1[CH:20]=[CH:21][C:22]([O:23][CH3:24])=[C:17]([F:16])[CH:18]=1)=[O:29])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 2734969(R)-4-Benzyl-2-oxazolidinoneHCID 901181402-(3-Fluoro-4-methoxy-phenyl)-cyclopropanecarbonyl chloride

Product 1

HCID 90118203(R)-4-benzyl-3-[2-(3-fluoro-4-methoxy-phenyl)-cyclopropanecarbonyl]-oxazolidin-2-on

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

After (R)-4-benzyl-oxazolidin-2-on (0.858 g, 4.84 mmol) was dissolved in anhydrous THF (15 mL), NaH (0.226 g, 5.64 mmol) was added thereto, and the mixture was stirred for 30 minutes. 2-(3-Fluoro-4-methoxy-phenyl)-cyclopropanecarbonyl chloride obtained in Step B was added thereto at −78° C., and the mixture was stirred for 15 minutes, and then stirred at room temperature for 2 hours. After the termination of the reaction, the reactant was added with NH4Cl and extracted with ethyl acetate. The organic layer was separated, dried with anhydrous magnesium sulfate, concentrated under reduced pressure, and purified by column chromatography (eluent, EtOAc/Hex/MC=1/5/10) to obtain the title compounds [(more polar, 33 mg, 49%), (less polar, 33 mg, 49%)].

Workup

  1. stirringat −78° C., and the mixture was stirred for 15 minutes
  2. stirringstirred at room temperature for 2 hours
  3. customAfter the termination of the reaction
  4. extractionextracted with ethyl acetate
  5. customThe organic layer was separated
  6. dry with materialdried with anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. custompurified by column chromatography (eluent, EtOAc/Hex/MC=1/5/10)

Sources & evidence

ORD record
ord-0931f7c2b1b54eb8bf16268b288ef0ce
Source dataset
uspto-grants-2016_09
Patent number
US09447044B2

Reaction notes

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