Chloroform → HCID 15573409, compound

HRID 2106930Notes

Reaction equation

HRID 2106930 reaction equation
[O:1]([CH2:8][C:9]([NH:11][CH:12]1[C:29](=[O:30])[N:14]2[CH:15]([C:21]([O:23][CH2:24][C:25]([Cl:28])([Cl:27])[Cl:26])=[O:22])[C:16]([CH3:20])([CH2:18]Br)[S:17][C@H:13]12)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)(Cl)Cl>N1C=CC=CC=1>[O:1]([CH2:8][C:9]([NH:11][CH:12]1[C:29](=[O:30])[N:14]2[C:15]([C:21]([O:23][CH2:24][C:25]([Cl:27])([Cl:26])[Cl:28])=[O:22])=[C:16]([CH3:18])[CH2:20][S:17][C@H:13]12)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=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 phosphoric acid and water in order, dried and then concentrated. The residue was subjected to chromatography on silica gel and eluated 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, dilute phosphoric acid and water in order
  5. customdried
  6. concentrationconcentrated
  7. customto yield an oil
  8. customThe oil was crystallized from a mixture of acetone and petroleum ether

Sources & evidence

ORD record
ord-8fda4ab3ed4e4a3e82a7c3a47fcd0f11
Source dataset
uspto-grants-1990_06
Patent number
US04931555

Reaction notes

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