Methyl iodide → HCID 66981144, compound

HRID 2279253Notes

Reaction equation

HRID 2279253 reaction equation
[O:1]=[C:2]1[NH:6][CH2:5][C@H:4]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[N:3]1[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18].[H-].[Na+].[CH3:26]I.[NH4+].[Cl-]>C1COCC1>[CH3:26][N:6]1[CH2:5][C@H:4]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[N:3]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C:2]1=[O:1]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 86693760HCID 86693760, compound

Product 1

HCID 66981144HCID 66981144, compoundYield 67.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (R)-benzyl 2-oxooxazolidine-5-carboxylate (25a) (0.1 g 0.312 mmol) in THF (2 mL), cooled to 0° C., Sodium hydride (13.9 mg, 0.37 mmol, 50% dispersion in mineral oil) was added and stirred for 60 min. MeI (0.048 g, 0.343 mmol) was added drop-wise to the reaction mixture, slowly warmed to room temperature and stirred for further 2 h. After completion (by TLC), the reaction mixture was poured into saturated NH4Cl solution (10 mL) and extracted with EtOAc (2×5 mL). The combined organic extracts were dried over Na2SO4 and concentrated under reduced pressure to provide the crude residue which was purified by column chromatography to afford 25b (0.070 g, 67%) as a brown syrup.

Workup

  1. stirringstirred for further 2 h
  2. extractionextracted with EtOAc (2×5 mL)
  3. dry with materialThe combined organic extracts were dried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customto provide the crude residue which
  6. customwas purified by column chromatography

Sources & evidence

ORD record
ord-1dd6b2d083a942c2a0852aefc59157d6
Source dataset
uspto-grants-2015_09
Patent number
US09133182B2

Reaction notes

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