Pyridine → HCID 70590894, compound

HRID 1856360Notes

Reaction equation

HRID 1856360 reaction equation
[N+:1]([C:4]1[CH:25]=[CH:24][CH:23]=[CH:22][C:5]=1[CH2:6][O:7][C:8]([NH:10][C@@H:11]1[C:18](=[O:19])[N:17]2[C@@H:12]1[CH2:13][CH2:14][O:15][C:16]2(C)[CH3:20])=[O:9])([O-:3])=[O:2].C(Cl)(=[O:28])C.N1C=CC=CC=1>FC(F)(F)C(O)=O.O.C(Cl)Cl>[N+:1]([C:4]1[CH:25]=[CH:24][CH:23]=[CH:22][C:5]=1[CH2:6][O:7][C:8]([NH:10][C@H:11]1[C@H:12]([CH2:13][CH2:14][O:15][C:16](=[O:28])[CH3:20])[NH:17][C:18]1=[O:19])=[O:9])([O-:3])=[O:2]

Participants

7

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 86737153HCID 86737153, compound

Product 1

HCID 70590894HCID 70590894, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
0 °C

Procedure

A quantity (3.49 g) of trans-7-[o-nitrobenzyloxycarbonylamino]-8-oxo-2,2-dimethyl-3-oxa-1-azabicyclo[4.2.0]octane is dissolved in 10 ml of 2:1 mixture of trifluoroacetic acid and water. After standing at 25° C. for 10 min. most of the solvent is removed in vacuo at 25°. The residue is taken up in 50 ml of benzene and evaporated to dryness in vacuo at 25°. The last step is repeated four more times to give a residue which is taken up in 100 ml of methylene chloride and cooled to 0° C.; whereupon 0.9 ml of acetyl chloride and 1 ml of pyridine are added dropwise. After stirring 1 hour at 0° C., the resulting solution is washed with 3×50 ml of brine and dried over anhydrous magnesium sulfate. The solvent is removed and the residue is chromatographed to give trans-3-[o-nitrobenzyloxycarbonylamino]-4-[2-acetoxyethyl]-2-azetidinone (1.85 g).

Workup

  1. customis removed in vacuo at 25°
  2. customevaporated to dryness in vacuo at 25°
  3. customto give a residue which
  4. washthe resulting solution is washed with 3×50 ml of brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent is removed
  7. customthe residue is chromatographed

Sources & evidence

ORD record
ord-4ff656b2ed954de28655752088ae3183
Source dataset
uspto-grants-1980_08
Patent number
US04218459

Reaction notes

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