Acetic Anhydride → Benzyl 6-azido-3-acetoxyl-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate

HRID 1154919Notes

Reaction equation

HRID 1154919 reaction equation
[N:1]([CH:4]1[C:10](=[O:11])[N:9]2[CH:5]1[CH2:6][C:7](=[O:22])[CH:8]2[C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])=[N+:2]=[N-:3].[C:23](OC(=O)C)(=[O:25])[CH3:24]>N1C=CC=CC=1>[N:1]([CH:4]1[C:10](=[O:11])[N:9]2[CH:5]1[CH2:6][C:7]([O:22][C:23]([CH3:24])=[O:25])=[C:8]2[C:12]([O:14][CH2:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)=[O:13])=[N+:2]=[N-:3]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 20563654Benzyl 6-azido-1-azabicyclo[3.2.0]-heptan-3,7-dione-2-carboxylate

Product 1

HCID 20563675Benzyl 6-azido-3-acetoxyl-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of benzyl 6-azido-1-azabicyclo[3.2.0]heptan-3,7-dione-2-carboxylate (1 mmol) and acetic anhydride (10 mmol) in anhydrous pyridine (1 ml) is kept at 0°-5° C. for 3 days. The solution is concentrated under vacuum, diluted with ethyl acetate, washed with water, pH 2 buffer, 5% sodium bicarbonate solution, and brine, dried with magnesium sulfate, filtered, and evaporated under vacuum to give benzyl 6-azido-3-acetoxyl-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate.

Workup

  1. concentrationThe solution is concentrated under vacuum
  2. additiondiluted with ethyl acetate
  3. washwashed with water, pH 2 buffer
  4. dry with material5% sodium bicarbonate solution, and brine, dried with magnesium sulfate
  5. filtrationfiltered
  6. customevaporated under vacuum

Sources & evidence

ORD record
ord-0694947f97044055b320a4f3e926c594
Source dataset
uspto-grants-1981_11
Patent number
US04298741

Reaction notes

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