Triethylamine → HCID 57261035, compound

HRID 850289Notes

Reaction equation

HRID 850289 reaction equation
[CH2:1]([N:8]1[C:15](=[O:16])[C@@H:14]([OH:17])[C@H:13]2[C@@H:9]1[CH2:10][CH2:11][O:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:25][S:26](Cl)(=[O:28])=[O:27]>C(Cl)Cl.O>[CH2:1]([N:8]1[C:15](=[O:16])[C@@H:14]([O:17][S:26]([CH3:25])(=[O:28])=[O:27])[C@H:13]2[C@@H:9]1[CH2:10][CH2:11][O:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 56975018HCID 56975018, compound

Product 1

HCID 57261035HCID 57261035, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

15 g of the (1R*,5S*,8S*)-6-benzyl-8-hydroxy-7-oxo-2-oxa-6-azabicyclo[3.3.0]octane obtained in the step 2 of Example A was added to 300 ml of methylene chloride, and cooled with ice. To this mixture was added 16.3 ml of triethylamine. Then, 7.5 ml of methanesulfonyl chloride was added dropwise thereto, followed by stirring overnight. Thereafter, water and methylene chloride were added to the reaction mixture so as to extract the desired product in an organic layer. After this organic layer was dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure to obtain 20.6 g of (1R*,5S*,8S*)-6-benzyl-8-mesyloxy-7-oxo-2-oxa-6-azabicyclo[3.3.0]octane.

Workup

  1. temperaturecooled with ice
  2. extractionto extract the desired product in an organic layer
  3. dry with materialAfter this organic layer was dried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-643a1121a8104ba18e3c1f6377a89136
Source dataset
uspto-grants-2000_01
Patent number
US06017911

Reaction notes

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