Triethylamine → HCID 11448209, compound

HRID 2041968Notes

Reaction equation

HRID 2041968 reaction equation
[OH:1][CH:2]1[CH2:5][N:4]([C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:7])[CH2:3]1.[CH3:14][S:15](Cl)(=[O:17])=[O:16].C(N(CC)CC)C>C1COCC1>[CH3:14][S:15]([O:1][CH:2]1[CH2:3][N:4]([C:6](=[O:7])[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:5]1)(=[O:17])=[O:16]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 20352194(3-hydroxyazetidin-1-yl)(phenyl)Methanone

Product 1

HCID 11448209HCID 11448209, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of (3-hydroxyazetidin-1-yl)(phenyl)methanone (13.5 g, 76.2 mmol), methanesulfonyl chloride (12.6 g, 110 mmol) and triethylamine (12.3 g, 121 mmol) in THF (300 ml) was heated at 50° C. for 3 h. Then, the reaction mixture was cooled to room temperature and the resulting precipitate was collected by filtration. The filtrate was concentrated under reduced pressure, the residue was partitioned between ethyl acetate and water and separated. The organic layer was washed with saturated sodium chloride, dried (Na2SO4), filtered and concentrated under reduced pressure. The residue was purified by flash column chromatography (silica gel, 50:50 to 80:20, ethyl acetate/heptane) provided 1-benzoylazetidin-3-yl methanesulfonate (12.8 g, 66%) as a white solid.

Workup

  1. filtrationthe resulting precipitate was collected by filtration
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. customthe residue was partitioned between ethyl acetate and water
  4. customseparated
  5. washThe organic layer was washed with saturated sodium chloride
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by flash column chromatography (silica gel, 50:50 to 80:20, ethyl acetate/heptane)

Sources & evidence

ORD record
ord-abbfbceacc8e41d0a9d94bca0dc1b632
Source dataset
uspto-grants-2013_11
Patent number
US08586571B2

Reaction notes

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