Methanesulfonyl chloride → HCID 118103467, compound

HRID 1051750Notes

Reaction equation

HRID 1051750 reaction equation
CS(Cl)(=O)=O.C(=O)(O)[O-].[Na+].[NH2:11][CH:12]([CH2:17][C:18]1[CH:23]=[C:22]([F:24])[C:21]([F:25])=[CH:20][C:19]=1[F:26])[CH2:13][C:14](O)=[O:15]>C(#N)C>[F:26][C:19]1[CH:20]=[C:21]([F:25])[C:22]([F:24])=[CH:23][C:18]=1[CH2:17][CH:12]1[NH:11][C:14](=[O:15])[CH2:13]1

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 231460233-Amino-4-(2,4,5-trifluorophenyl)butanoic acid

Product 1

HCID 118103467HCID 118103467, compoundYield 96.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To the rapidly stirred 80° C. suspension of methanesulfonyl chloride (0.88 g, 7.72 mmol) and sodium bicarbonate (3.24 g, 38.6 mmol) in acetonitrile (400 mL), 3-amino-4-(2,4,5-trifluorophenyl)butanoic acid ((±)-Ia, 1.5 g, 6.43 mmol) is added over period of 2 h. The resulting suspension was further stirred for 16 h at 80° C., after which time the fine suspension was cooled to 0° C. and filtered. The filtrate was evaporated under reduced pressure to afford 1.34 g (96% yield) of racemic 4-(2,4,5-trifluorobenzyl)azetidin-2-one ((±)-IIa) as pale yellow crystalline solid.

Workup

  1. additionis added over period of 2 h
  2. temperatureafter which time the fine suspension was cooled to 0° C.
  3. filtrationfiltered
  4. customThe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-4ed0499a4ea74ce0a773a8c3de95cb9f
Source dataset
uspto-grants-2016_07
Patent number
US09388188B2

Reaction notes

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