Triethylamine → 1-(4-Morpholinocarbonyl-1,3-thiazol-2-yl)-3-methanesulfonyloxyazetidine

HRID 891562Notes

Reaction equation

HRID 891562 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]([C:9]2[N:10]=[C:11]([N:14]3[CH2:17][CH:16]([OH:18])[CH2:15]3)[S:12][CH:13]=2)=[O:8])[CH2:3][CH2:2]1.[CH3:19][S:20](Cl)(=[O:22])=[O:21].C(N(CC)CC)C>C(Cl)Cl>[O:1]1[CH2:2][CH2:3][N:4]([C:7]([C:9]2[N:10]=[C:11]([N:14]3[CH2:17][CH:16]([O:18][S:20]([CH3:19])(=[O:22])=[O:21])[CH2:15]3)[S:12][CH:13]=2)=[O:8])[CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 222428331-(4-Morpholinocarbonyl-1,3-thiazol-2-yl)-3-hydroxyazetidine

Product 1

HCID 222429461-(4-Morpholinocarbonyl-1,3-thiazol-2-yl)-3-methanesulfonyloxyazetidineYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(4-morpholinocarbonyl-1,3-thiazol-2-yl)-3-hydroxyazetidine (540 mg, 2.01 mmol) (obtained as described in Reference Example 11(2)) in methylene chloride (27 ml) were added methanesulfonyl chloride (0.467 ml, 6.03 mmol) and triethylamine (0.845 ml, 6.03 mmol) in an ice bath. The reaction mixture was brought to room temperature in 10 minutes, and stirred for 1 hour. After checking the completion of the reaction, the reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium hydrogencarbonate solution. The obtained organic layer was washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column using 5% methanol in ethyl acetate as the eluant to afford 1-(4-morpholinocarbonyl-1,3-thiazol-2-yl)-3-methanesulfonyloxyazetidine (688 mg, yield 99%) as a pale yellow solid.

Workup

  1. customthe completion of the reaction
  2. customthe reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium hydrogencarbonate solution
  3. washThe obtained organic layer was washed with saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-e148da1b0de34c2fa0df387431d94913
Source dataset
uspto-grants-2006_02
Patent number
US07001897B2

Reaction notes

Loading…