(Diethylamino)sulfur trifluoride → [(1S,2S)-1-(3-fluoro-azetidine-1-carbonyl)-2-methyl-butyl]-carbamic acid tert-butyl ester

HRID 49762Notes

Reaction equation

HRID 49762 reaction equation
C(N(S(F)(F)[F:7])CC)C.[C:10]([O:14][C:15](=[O:29])[NH:16][C@H:17]([C:22]([N:24]1[CH2:27][CH:26](O)[CH2:25]1)=[O:23])[C@@H:18]([CH3:21])[CH2:19][CH3:20])([CH3:13])([CH3:12])[CH3:11]>ClCCl.C(OCC)(=O)C>[C:10]([O:14][C:15](=[O:29])[NH:16][C@H:17]([C:22]([N:24]1[CH2:27][CH:26]([F:7])[CH2:25]1)=[O:23])[C@@H:18]([CH3:21])[CH2:19][CH3:20])([CH3:13])([CH3:12])[CH3:11]

Participants

5

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 69872277Tert-butyl (2S,3S)-1-(3-hydroxyazetidin-1-yl)-3-methyl-1-oxopentan-2-ylcarbamate

Product 1

HCID 69871849[(1S,2S)-1-(3-fluoro-azetidine-1-carbonyl)-2-methyl-butyl]-carbamic acid tert-butyl esterYield 25%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a cooled (−78° C.) solution of diethylaminosulfur trifluoride (0.46 mL, 3.5 mmol) in dichloromethane (6 mL), was added dropwise a solution of [(1S,2S)-1-(3-hydroxy-azetidine-1-carbonyl)-2-methyl-butyl]-carbamic acid tert-butyl ester (1.0 g, 3.5 mmol) in dichloromethane (4 mL). The mixture was warmed to room temperature, stirred overnight, then diluted with ethyl acetate and poured into ice/water. The layers were separated, and the organic phase washed with water and brine, dried over magnesium sulfate and concentrated. The product was purified by flash-chromatography (ethyl acetate) and isolated as an oil (250 mg, 25%).

Workup

  1. customThe layers were separated
  2. washthe organic phase washed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe product was purified by flash-chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-27a06b4544a5464f8d48b3adced3fb97
Source dataset
uspto-grants-2004_03
Patent number
US06710040B1

Reaction notes

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