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

HRID 2234756Notes

Reaction equation

HRID 2234756 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-8b06519c7f18412d8da172fd10bbda06
Source dataset
uspto-grants-2010_05
Patent number
US07713950B2

Reaction notes

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