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

HRID 620419Notes

Reaction equation

HRID 620419 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.[CH3:22]CN(CC)CC.[N:29]12[C:35](=[O:36])[CH2:34][CH:33]1[CH2:32][C:31](=O)[CH:30]2[C:38]([O:40][CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)=[O:39]>C(Cl)Cl>[C:19]1([CH3:22])[C:14]([S:11]([O:10][C:31]2[CH2:32][CH:33]3[N:29]([C:35](=[O:36])[CH2:34]3)[C:30]=2[C:38]([O:40][CH2:41][C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)=[O:39])(=[O:12])=[O:13])=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 77773Toluene-p-sulphonic anhydrideHCID 12804725Benzyl 3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylate

Product 1

HCID 131712683Benzyl 3-toluenesulfonyloxy-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

p-Toluenesulfonic anhydride (33 mg, 0.1 mmol) and Et3N (17 μl, 0.12 mmol) are added to a solution of benzyl 1-azabicyclo[3.2.0]heptan-3,7-dione-2-carboxylate (26 mg., 0.1 mmol) in anhydrous CH2Cl2 (2 ml). The resulting solution is stirred at room temperature for 2 hours. The mixture is diluted with CH2Cl2 (10 ml), washed with H2O (2×5 ml), pH 3 phosphate buffer (5 ml) and 5% NaHCO3 (5 ml), dried with MgSO4, filtered and evaporated i.v. to provide benzyl 3-toluenesulfonyloxy-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate.

Workup

  1. washwashed with H2O (2×5 ml), pH 3 phosphate buffer (5 ml) and 5% NaHCO3 (5 ml)
  2. dry with materialdried with MgSO4
  3. filtrationfiltered
  4. customevaporated i.v

Sources & evidence

ORD record
ord-c876ad95c66f432392d09e480e63f80d
Source dataset
uspto-grants-1989_04
Patent number
US04820817

Reaction notes

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