(Diethylamino)sulfur trifluoride → tert-Butyl(4S,5R)-4-(fluoromethyl)-2,2-dimethyl-5-[4-(fluoromethylthio)phenyl]-1,3-oxazolidine-3-carboxylate

HRID 901076

Reaction equation

HRID 901076 reaction equation
C(N(S(F)(F)[F:7])CC)C.[F:10][CH2:11][C@@H:12]1[C@@H:16]([C:17]2[CH:22]=[CH:21][C:20]([S:23]([CH3:25])=O)=[CH:19][CH:18]=2)[O:15][C:14]([CH3:27])([CH3:26])[N:13]1[C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29].C(=O)(O)[O-].[Na+]>ClCCl.[Sb](Cl)(Cl)Cl>[F:10][CH2:11][C@@H:12]1[C@@H:16]([C:17]2[CH:22]=[CH:21][C:20]([S:23][CH2:25][F:7])=[CH:19][CH:18]=2)[O:15][C:14]([CH3:27])([CH3:26])[N:13]1[C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29]

Participants

6

Reactant 3

HCID 123472(Diethylamino)sulfur trifluorideHCID 516892Sodium BicarbonateHCID 68720168tert-Butyl(4S,5R)-4-(fluoromethyl)-2,2-dimethyl-5-[4-(methylsulfinyl)phenyl]-1,3-oxazolidine-3-carboxylate

Product 1

HCID 68719639tert-Butyl(4S,5R)-4-(fluoromethyl)-2,2-dimethyl-5-[4-(fluoromethylthio)phenyl]-1,3-oxazolidine-3-carboxylateYield 86.5%

Reagents, catalysts & solvents 2

HCID 24814Antimony trichlorideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A solution of diethylamino sulfurtrifluoride (DAST), (9.34 g, 1.75 eq ) in 10 ml of dichloromethane was added drop wise to the solution of 14 (12.3 g) and antimony (III) chloride (0.23 g, 0.03 eq ) in 150 ml of dichloromethane (anhydrous) at −5° C., and the reaction mixture was warmed up to room temperature overnight. A cold saturated solution of sodium bicarbonate (80 ml) was added and stirred for 30 min and extracted with dichloromethane (100 ml×2). The organic layer was washed with a 10% solution of sodium bicarbonate and with brine (50 ml) and dried over sodium sulfate. After purification, via a column, 10.7 g of the desired product (as a heavy oil) was obtained.

Workup

  1. extractionextracted with dichloromethane (100 ml×2)
  2. washThe organic layer was washed with a 10% solution of sodium bicarbonate and with brine (50 ml)
  3. dry with materialdried over sodium sulfate
  4. customAfter purification

Sources & evidence

ORD record
ord-ebb033e654d74be2a94b18917bab6ff1
Source dataset
uspto-grants-2008_04
Patent number
US07361689B2

Linked notes

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