Hydrochloric Acid → HCID 12833966, compound

HRID 1764001Notes

Reaction equation

HRID 1764001 reaction equation
[Br-].[Al+3].[Br-].[Br-].[CH3:5][C:6]12[CH2:14][C:10]1([C:11]([OH:13])=[O:12])[N:9]1[C:15](=[O:27])[CH:16]([NH:17][C:18](=[O:26])[CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C@H:8]1[S:7]2.Cl>C(=S)=S>[CH3:5][CH:6]1[CH:14]=[C:10]([C:11]([OH:13])=[O:12])[N:9]2[C:15](=[O:27])[CH:16]([NH:17][C:18](=[O:26])[CH2:19][C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[C@H:8]2[S:7]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 166749BromhydrolHCID 705294222-Methyl-2,3-methylene-6-(2-phenylacetamido)penam-3-carboxylic acid

Product 1

HCID 12833966HCID 12833966, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent2×

Procedure

A solution of aluminum bromide (1.7 g.) in carbon disulfide (40 ml.) was dropwise added under stirring at room temperature to a suspension of 2-methyl-2,3-methylene-6-(2-phenylacetamido)penam-3-carboxylic acid (0.66 g.) in carbon disulfide (70 ml.) and the mixture was stirred for 20 hours at the same temperature. After the reaction was completed, the reaction mixture was poured into 5% hydrochloric acid (200 ml.) and the hydrochloric acid layer was separated and then extracted with ethyl acetate. The extract was washed with water and dried, after which the solvent was distilled off. The residue was recrystallized from acetonitrile to give 2-methyl-7-(2-phenylacetamido)-3-cephem-4-carboxylic acid (0.33 g.), mp 109° C. (dec.).

Workup

  1. customthe hydrochloric acid layer was separated
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water
  4. customdried
  5. distillationafter which the solvent was distilled off
  6. customThe residue was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-758303d8ca2a402bb2c0cc9c2a9bee3b
Source dataset
uspto-grants-1978_09
Patent number
US04113940

Reaction notes

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