Triethylamine → 3-Methanesulfonyloxy-1-[4-(3-methoxyazetidine-1-carbonyl)-1,3-oxazol-2-yl]azetidine

HRID 891814Notes

Reaction equation

HRID 891814 reaction equation
[OH:1][CH:2]1[CH2:5][N:4]([C:6]2[O:7][CH:8]=[C:9]([C:11]([N:13]3[CH2:16][CH:15]([O:17][CH3:18])[CH2:14]3)=[O:12])[N:10]=2)[CH2:3]1.[CH3:19][S:20](Cl)(=[O:22])=[O:21].C(N(CC)CC)C>C(Cl)Cl>[CH3:19][S:20]([O:1][CH:2]1[CH2:5][N:4]([C:6]2[O:7][CH:8]=[C:9]([C:11]([N:13]3[CH2:16][CH:15]([O:17][CH3:18])[CH2:14]3)=[O:12])[N:10]=2)[CH2:3]1)(=[O:22])=[O:21]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 222430243-Hydroxy-1-[4-(3-methoxyazetidine-1-carbonyl)-1,3-oxazol-2-yl]azetidine

Product 1

HCID 222428343-Methanesulfonyloxy-1-[4-(3-methoxyazetidine-1-carbonyl)-1,3-oxazol-2-yl]azetidineYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-hydroxy-1-[4-(3-methoxyazetidine-1-carbonyl)-1,3-oxazol-2-yl]azetidine (480 mg, 1.89 mmol) (obtained as described in Reference Example 73(2)) in methylene chloride (24 ml) were added methanesulfonyl chloride (439 μl, 5.67 mmol) and triethylamine (795 ml, 5.67 mmol) in an ice bath and the mixture was stirred for 10 minutes and then at room temperature for 30 minutes. After checking the completion of the reaction, the mixture was partitioned between ethyl acetate and saturated aqueous sodium hydrogencarbonate solution. The organic layer was washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium chloride, filtered and concentrated under reduced pressure. To the residue were added ethyl acetate and diisopropyl ether to give a solid and the solid was collected by filtration, washed with diisopropyl ether to afford 3-methanesulfonyloxy-1-[4-(3-methoxyazetidine-1-carbonyl)-1,3-oxazol-2-yl]azetidine (586 mg, yield 94%) as a pale yellow solid.

Workup

  1. waitat room temperature for 30 minutes
  2. customthe completion of the reaction
  3. customthe mixture was partitioned between ethyl acetate and saturated aqueous sodium hydrogencarbonate solution
  4. washThe organic layer was washed with saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous sodium chloride
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. additionTo the residue were added ethyl acetate and diisopropyl ether
  9. customto give a solid
  10. filtrationthe solid was collected by filtration
  11. washwashed with diisopropyl ether

Sources & evidence

ORD record
ord-57b1880c80b14247bf5044bc40d1f917
Source dataset
uspto-grants-2006_02
Patent number
US07001897B2

Reaction notes

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