Sodium hydride → (R)-4-benzyl-3-[2-(4-benzyloxy-3,5-difluoro-phenyl)-cyclopropanecarbonyl]-oxazolidin-2-on

HRID 62903Notes

Reaction equation

HRID 62903 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+].[CH2:16]([O:23][C:24]1[C:29]([F:30])=[CH:28][C:27]([CH:31]2[CH2:33][CH:32]2[C:34](Cl)=[O:35])=[CH:26][C:25]=1[F:37])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[NH4+].[Cl-]>C1COCC1>[CH2:1]([C@@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:34]([CH:32]1[CH2:33][CH:31]1[C:27]1[CH:26]=[C:25]([F:37])[C:24]([O:23][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[C:29]([F:30])[CH:28]=1)=[O:35])[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 90118321HCID 90118321, compound

Product 1

HCID 90118118(R)-4-benzyl-3-[2-(4-benzyloxy-3,5-difluoro-phenyl)-cyclopropanecarbonyl]-oxazolidin-2-on

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

After (R)-4-benzyl-oxazolidin-2-on (52 mg, 0.295 mmol) was dissolved in anhydrous THF (2 ml), NaH (60%, 14 mg, 0.344 mmol) was added thereto, and the mixture was stirred for 30 minutes. Next, 2-(4-benzyloxy-3,5-difluoro-phenyl)-cyclopropanecarnoyl chloride obtained in Step A was added thereto at −78° C., and the mixture was stirred for 15 minutes, and then stirred at room temperature for 1 hour. After the termination of the reaction, NH4Cl solution was added thereto and the mixture was 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=1/2) to obtain each title compound [(more polar, 41 mg, 36%), (less polar, 44 mg, 38%)].

Workup

  1. stirringat −78° C., and the mixture was stirred for 15 minutes
  2. stirringstirred at room temperature for 1 hour
  3. additionwas added
  4. extractionthe mixture was extracted 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=1/2)

Sources & evidence

ORD record
ord-18f9bfb743ed485cb7b64c8d3b938495
Source dataset
uspto-grants-2016_09
Patent number
US09447044B2

Reaction notes

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