Pyridine → HCID 15573412, compound

HRID 1903038Notes

Reaction equation

HRID 1903038 reaction equation
[C:1]1([CH2:7][C:8]([NH:10][CH:11]2[C:28](=[O:29])[N:13]3[CH:14]([C:20]([O:22][CH:23]([CH:25]4[CH2:27][CH2:26]4)[CH3:24])=[O:21])[C:15]([CH3:19])([CH2:17]Br)[S:16][C@H:12]23)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N1C=CC=CC=1>C1C=CC=CC=1>[C:1]1([CH2:7][C:8]([NH:10][CH:11]2[C:28](=[O:29])[N:13]3[C:14]([C:20]([O:22][CH:23]([CH:25]4[CH2:26][CH2:27]4)[CH3:24])=[O:21])=[C:15]([CH3:19])[CH2:17][S:16][C@H:12]23)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 1049PyridineHCID 70361134HCID 70361134, compound

Product 1

HCID 15573412HCID 15573412, compoundYield 62.5%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 1-cyclopropylethyl 6-(2-phenylacetamido)-2-methyl-2-bromomethylpenam-3-carboxylate (0.5 g.) and pyridine (0.20 g.) in benzene (12 cc) was heated under reflux for 3 hours. After cooling, the benzene layer was washed with water, dried and then concentrated. The residue was subjected to chromatography on silica gel to yield crystals (0.26 g.) of 1-cyclopropylethyl 7-(2-phenylacetamido)-3-methyl-3-cephem-4-carboxylate, m.p. 108°-112° C.

Workup

  1. temperatureunder reflux for 3 hours
  2. temperatureAfter cooling
  3. washthe benzene layer was washed with water
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-3e163e391c7a48088b97ffee7c9ab00e
Source dataset
uspto-grants-1984_03
Patent number
US04435321

Reaction notes

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