(Diethylamino)sulfur trifluoride → (4S)-4-(2-Fluoro-2-methylpropyl)-2-oxazolidinone

HRID 1880516Notes

Reaction equation

HRID 1880516 reaction equation
O[C:2]([CH3:11])([CH3:10])[CH2:3][C@H:4]1[CH2:8][O:7][C:6](=[O:9])[NH:5]1.C(N(S(F)(F)[F:18])CC)C.C([O-])(O)=O.[Na+]>ClCCl>[F:18][C:2]([CH3:11])([CH3:10])[CH2:3][C@H:4]1[CH2:8][O:7][C:6](=[O:9])[NH:5]1

Participants

5

Reactant 3

HCID 123472(Diethylamino)sulfur trifluorideHCID 516892Sodium BicarbonateHCID 11321109(S)-4-(2-Hydroxy-2-methylpropyl)oxazolidin-2-one

Product 1

HCID 11194496(4S)-4-(2-Fluoro-2-methylpropyl)-2-oxazolidinone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A dichloromethane solution (100 mL) of the alcohol (47.8 g) from Step 3 was added to a −70° C. solution of (diethylamino)sulfur trifluoride (48.5 g) in dichloromethane (500 mL). The mixture was warmed to room temperature and stirred for 1 hour. The mixture was then carefully added to a 0° C. mixture of saturated aqueous NaHCO3 (800 mL). The organic layer was separated and washed with saturated aqueous NaHCO3. The aqueous was further extracted with dichloromethane (100 mL) and the combined dichloromethane layers were dried and concentrated. The residue was purified by chromatography on SiO2 using ethyl acetate and hexanes (1:5) followed by ethyl acetate to yield (4S)-4-(2-fluoro-2-methylpropyl)-1,3-oxazolidin-2-one.

Workup

  1. additionThe mixture was then carefully added to a 0° C.
  2. customThe organic layer was separated
  3. washwashed with saturated aqueous NaHCO3
  4. extractionThe aqueous was further extracted with dichloromethane (100 mL)
  5. dry with materialthe combined dichloromethane layers were dried
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography on SiO2

Sources & evidence

ORD record
ord-b7c67e77288e49658c91062c0f11f3f8
Source dataset
uspto-grants-2012_11
Patent number
US08318748B2

Reaction notes

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