Acetic Anhydride → HCID 15136297, compound

HRID 1164335Notes

Reaction equation

HRID 1164335 reaction equation
[N:1]12[C:7](=[O:8])[CH2:6][CH:5]1[CH2:4][C:3](=[O:9])[CH:2]2[C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11].[CH3:20][C:21](OC(C)=O)=[O:22]>N1C=CC=CC=1>[C:21]([O:9][C:3]1[CH2:4][CH:5]2[N:1]([C:7](=[O:8])[CH2:6]2)[C:2]=1[C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11])(=[O:22])[CH3:20]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 12804725Benzyl 3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylate

Product 1

HCID 15136297HCID 15136297, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of benzyl 1-azabicyclo[3.2.0]heptan-3,7-dione-2-carboxylate (20 mg) in anhydrous pyridine (200 μl) and Ac2O (100 μl) is kept at 0° C. for 8 hrs. The mixture is evaporated in vacuo and the residue dissolved in EtOAc. This solution is washed with pH 2 phosphate buffer, 5% NaHCO3, and brine, dried with MgSO4, filtered, and evaporated i.v. to provide benzyl 3-acetoxy-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate. By substituting Ac2O with ##STR25## in Method B, various 3-acyloxy derivatives are obtained.

Workup

  1. customThe mixture is evaporated in vacuo
  2. dissolutionthe residue dissolved in EtOAc
  3. washThis solution is washed with pH 2 phosphate buffer, 5% NaHCO3, and brine
  4. dry with materialdried with MgSO4
  5. filtrationfiltered
  6. customevaporated i.v

Sources & evidence

ORD record
ord-0eb302ca56ff44abaa0b8023c37c837b
Source dataset
uspto-grants-1983_01
Patent number
US04369187

Reaction notes

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