Methanesulfonyl chloride → HCID 18343025, compound

HRID 237490Notes

Reaction equation

HRID 237490 reaction equation
[NH:1]1[CH2:4][CH:3]([OH:5])[CH2:2]1.CCN(C(C)C)C(C)C.[CH3:15][S:16](Cl)(=[O:18])=[O:17]>O1CCCC1>[CH3:15][S:16]([O:5][CH:3]1[CH2:4][N:1]([S:16]([CH3:15])(=[O:18])=[O:17])[CH2:2]1)(=[O:18])=[O:17]

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 15142903-Hydroxyazetidine

Product 1

HCID 18343025HCID 18343025, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Azetidin-3-ol (3.3 g) and DIPEA (20 mL) are dissolved in dry tetrahydrofuran (40 mL). After 30 min the reaction mixture is cooled to 0° C. and methanesulfonyl chloride (10.9 g) is added dropwise. After stirring for 2 hours at ambient temperature, the mixture is concentrated under vacuum, partitioned between ethyl acetate and water. The organic phase is dried (MgSO4) and concentrated. Chromatography of the residue on silica gel (cyclohexane/ethyl acetate 70:30) gives the title compound. Yield: 5 g.

Workup

  1. concentrationthe mixture is concentrated under vacuum
  2. custompartitioned between ethyl acetate and water
  3. dry with materialThe organic phase is dried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-abacf6cbd49b40a4aa0a39b0168661ae
Source dataset
uspto-grants-2014_02
Patent number
US08642585B2

Reaction notes

Loading…