Benzene → 7-[2-(2-Aminothiazol-4-yl)acetamido]-3-methylthiomethyl-3-cephem-4-carboxylic acid

HRID 1200123Notes

Reaction equation

HRID 1200123 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][C:8]([NH:10][CH:11]2[C:37](=[O:38])[N:13]3[C:14]([C:21]([O:23]C(C4C=CC=CC=4)C4C=CC=CC=4)=[O:22])=[C:15]([CH2:18][S:19][CH3:20])[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1.FC(F)(F)C(O)=O.C1(OC)C=CC=CC=1.C1C=CC=CC=1>C(Cl)Cl>[NH2:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][C:8]([NH:10][CH:11]2[C:37](=[O:38])[N:13]3[C:14]([C:21]([OH:23])=[O:22])=[C:15]([CH2:18][S:19][CH3:20])[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1

Participants

6

Reactant 4

HCID 241BenzeneHCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 88378350Benzhydryl 7-[2-(2-aminothiazol-4-yl) acetamido]-3-methylthiomethyl-3-cephem-4-carboxylate

Product 1

HCID 883784097-[2-(2-Aminothiazol-4-yl)acetamido]-3-methylthiomethyl-3-cephem-4-carboxylic acidYield 40.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
10 °C

Procedure

The mixture of benzhydryl 7-[2-(2-aminothiazol-4-yl)acetamido]-3-methylthiomethyl-3-cephem-4-carboxylate (3.3 g), trifluoroacetic acid (10 ml) and anisole (10 ml) in methylene chloride (10 ml) was stirred at 10° C. for an hour. After benzene (50 ml) was added to the reaction mixture, the trifluoroacetic acid therein was azeotropically removed under reduced pressure. The remained aqueous solution was poured into a mixture of ethyl acetate (100 ml) and water (100 ml), followed by adjusting to pH 7.5 with sodium bicarbonate. After separating out the aqueous solution, the organic solvent was removed therefrom by evaporation completely under reduced pressure, followed by adjusting to pH 3.0 with 10% hydrochloric acid. The precipitated solid was collected by filtration and then dried to give 7-[2-(2-aminothiazol-4-yl)acetamido]-3-methylthiomethyl-3-cephem-4-carboxylic acid (0.95 g).

Workup

  1. customthe trifluoroacetic acid therein was azeotropically removed under reduced pressure
  2. additionThe remained aqueous solution was poured into a mixture of ethyl acetate (100 ml) and water (100 ml)
  3. customAfter separating out the aqueous solution
  4. customthe organic solvent was removed
  5. customby evaporation completely under reduced pressure
  6. filtrationThe precipitated solid was collected by filtration
  7. customdried

Sources & evidence

ORD record
ord-7155ca6ac27648e9852a8ec5c109e733
Source dataset
uspto-grants-1990_02
Patent number
US04904652

Reaction notes

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