Chloroform → HCID 15573409, compound

HRID 1730705Notes

Reaction equation

HRID 1730705 reaction equation
[Cl:1][C:2]([Cl:30])([Cl:29])[CH2:3][O:4][C:5]([CH:7]1[N:11]2[C:12](=[O:25])[CH:13]([NH:14][C:15](=[O:24])[CH2:16][O:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C@H:10]2[S:9][C:8]1([CH3:28])[CH2:26]Br)=[O:6].C(Cl)(Cl)Cl>N1C=CC=CC=1>[O:17]([CH2:16][C:15]([NH:14][CH:13]1[C:12](=[O:25])[N:11]2[C:7]([C:5]([O:4][CH2:3][C:2]([Cl:30])([Cl:29])[Cl:1])=[O:6])=[C:8]([CH3:28])[CH2:26][S:9][C@H:10]12)=[O:24])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 6212ChloroformHCID 70361141HCID 70361141, compound

Product 1

HCID 15573409HCID 15573409, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 2,2,2-trichloroethyl-6-(2-phenoxyacetamido)-2-methyl-2-bromomethylpenam-3-carboxylate (500 mg.), chloroform (10 cc) and pyridine (170 mg.) was heated under reflux for 10 hours. After cooling, the reaction mixture was washed with water, dilute phorphoric acid and water in order, dried and then concentrated. The residue was subjected to chromatography on silica gel and eluted to yield an oil. The oil was crystallized from a mixture of acetone and petroleum ether to yield 2,2,2-trichloroethyl 7-(2-phenoxyacetamido)-3-methyl-3-cephem-4-carboxylate, m.p. 111° - 113° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 10 hours
  3. temperatureAfter cooling
  4. washthe reaction mixture was washed with water
  5. additiondilute phorphoric acid and water in order
  6. customdried
  7. concentrationconcentrated
  8. washeluted
  9. customto yield an oil
  10. customThe oil was crystallized from a mixture of acetone and petroleum ether

Sources & evidence

ORD record
ord-a0b9fa5f3f2e4fa2be3ed9c72bc2f2dc
Source dataset
uspto-grants-1976_11
Patent number
US03993646

Reaction notes

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