(Bis(2-methoxyethyl)amino)sulfur trifluoride → (1R,5R)-7-Fluoro-4-oxo-3-[(1R)-1-phenylethyl]-3-azabicyclo[3.3.0]octan-1-ylcarboxylic acid tert-butyl ester

HRID 1917344Notes

Reaction equation

HRID 1917344 reaction equation
[C:1]([O:5][C:6]([C@@:8]12[CH2:15][CH:14](O)[CH2:13][C@@H:12]1[C:11](=[O:17])[N:10]([C@@H:18]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH3:19])[CH2:9]2)=[O:7])([CH3:4])([CH3:3])[CH3:2].COCCN(S(F)(F)[F:36])CCOC>C(Cl)Cl>[C:1]([O:5][C:6]([C@:8]12[CH2:15][CH:14]([F:36])[CH2:13][C@H:12]1[C:11](=[O:17])[N:10]([C@@H:18]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH3:19])[CH2:9]2)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 2734690(Bis(2-methoxyethyl)amino)sulfur trifluorideHCID 67491063(1S,5S)-7-Hydroxy-4-oxo-3-[(1R)-1-phenylethyl]-3-azabicyclo[3.3.0]octan-1-ylcarboxylic acid tert-butyl ester

Product 1

HCID 67491056(1R,5R)-7-Fluoro-4-oxo-3-[(1R)-1-phenylethyl]-3-azabicyclo[3.3.0]octan-1-ylcarboxylic acid tert-butyl esterYield 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(1S,5S)-7-Hydroxy-4-oxo-3-[(1R)-1-phenylethyl]-3-azabicyclo[3.3.0]octan-1-ylcarboxylic acid tert-butyl ester (1.0 g, 2.89 mmol) was dissolved in methylene chloride (15 mL). Bis(2-methoxyethyl)aminosulfur trifluoride (BAST) (0.59 mL) was added under ice-cooling, and the mixture was stirred at the same temperature for one hour. The reaction solution was washed with saturated sodium bicarbonate water, dried over magnesium sulfate, and filtered. Then, the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (hexane:ethyl acetate=10:1→4:1→1:1) to give 711 mg (71%) of the title compound as a colorless oil.

Workup

  1. temperaturecooling
  2. washThe reaction solution was washed with saturated sodium bicarbonate water
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customThen, the solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel chromatography (hexane:ethyl acetate=10:1→4:1→1:1)

Sources & evidence

ORD record
ord-f04276c0ba33455088a1a1ad260ff00d
Source dataset
uspto-grants-2013_12
Patent number
US08618094B2

Reaction notes

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