Hydrochloric Acid → HCID 12833966, compound

HRID 851581Notes

Reaction equation

HRID 851581 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-9d800a8c5b7d4a16a0d278634e8b63fa
Source dataset
uspto-grants-1983_05
Patent number
US04385176

Reaction notes

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