Triethylamine → Benzyl 6-azido-3-toluenesulfonyloxy-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate

HRID 1856072Notes

Reaction equation

HRID 1856072 reaction equation
C1(C)C=CC(S([O:10][S:11]([C:14]2[CH:19]=[CH:18][C:17](C)=[CH:16][CH:15]=2)(=[O:13])=[O:12])(=O)=O)=CC=1.[CH2:22](N(CC)CC)C.[N:29]([CH:32]1[C:38](=[O:39])[N:37]2[CH:33]1[CH2:34][C:35](=O)[CH:36]2[C:40]([O:42][CH2:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)=[O:41])=[N+:30]=[N-:31]>C(Cl)Cl>[N:29]([CH:32]1[C:38](=[O:39])[N:37]2[CH:33]1[CH2:34][C:35]([O:10][S:11]([C:14]1[C:15]([CH3:22])=[CH:16][CH:17]=[CH:18][CH:19]=1)(=[O:13])=[O:12])=[C:36]2[C:40]([O:42][CH2:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)=[O:41])=[N+:30]=[N-:31]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 77773Toluene-p-sulphonic anhydrideHCID 20563654Benzyl 6-azido-1-azabicyclo[3.2.0]-heptan-3,7-dione-2-carboxylate

Product 1

HCID 131711852Benzyl 6-azido-3-toluenesulfonyloxy-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

p-Toluenesulfonic anhydride (1 mmol) and triethylamine (1.2 mmol) are added to an ice-cold solution of benzyl 6-azido-1-azabicyclo[3.2.0]-heptan-3,7-dione-2-carboxylate (1 mmol) in anhydrous methylene chloride (10 ml). After stirring in the cold for 2 hr, the solution is washed with water, pH 3 phosphate buffer, and 5% sodium bicarbonate solution, dried over magnesium sulfate, filtered, and evaporated under vacuum to give benzyl 6-azido-3-toluenesulfonyloxy-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate.

Workup

  1. washthe solution is washed with water, pH 3 phosphate buffer, and 5% sodium bicarbonate solution
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated under vacuum

Sources & evidence

ORD record
ord-7e09c785f8ca4e15984c00d0050957ae
Source dataset
uspto-grants-1980_08
Patent number
US04217453

Reaction notes

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