Chloroform → HCID 15573409, compound

HRID 647777Notes

Reaction equation

HRID 647777 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-36e0d24527b54da4a99372d730bff0d6
Source dataset
uspto-grants-1983_10
Patent number
US04410458

Reaction notes

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