Pyridine → HCID 9904687, compound

HRID 1109814Notes

Reaction equation

HRID 1109814 reaction equation
[N+:1]([C:4]1[CH:26]=[CH:25][C:7]([CH2:8][O:9][C:10]([N:12]2[CH2:16][C@H:15](OS(C)(=O)=O)[CH2:14][C@H:13]2[C:22](=[S:24])[OH:23])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].N1C=CC=CC=1>C(Cl)Cl>[N+:1]([C:4]1[CH:26]=[CH:25][C:7]([CH2:8][O:9][C:10]([N:12]2[CH2:16][C@@H:15]3[CH2:14][C@H:13]2[C:22](=[O:23])[S:24]3)=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 1049PyridineHCID 178505330HCID 178505330, compound

Product 1

HCID 9904687HCID 9904687, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of crude (2S,4R)-1-p-nitrobenzyloxycarbonyl -4-methanesulfonyloxy-2-pyrrolidinethiocarboxylic acid (4.0 g) obtained in Example 8 in methylene chloride (40 ml) was added pyridine (1.91 g). The mixture was heated under refluxing for 7 hours. After the reaction was over, the mixture was washed with aqueous 1 mole/1 hydrochloric acid solution. The organic layer was dried over magnesium sulfate. After the solvent was distilled, residue was purified by silica gel chromatography to give (1S,4S)-5-p-nitrobenzyloxycarbonyl-2-thia-5-azabicyclo-[2.2.1]heptan-3-one.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder refluxing for 7 hours
  3. washwas washed with aqueous 1 mole/1 hydrochloric acid solution
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. distillationAfter the solvent was distilled
  6. customresidue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-b7c750efd0ca425fa285ac20c585a737
Source dataset
uspto-grants-1994_06
Patent number
US05322952

Reaction notes

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