Carbon Tetrachloride → 7-Amino-3-methoxymethyl-3-cephem-4-carboxylic acid
Reaction equation
C(Cl)(Cl)(Cl)Cl.C[C:7]([O:9][CH2:10][C:11]1[CH2:20][S:19][C@@H:14]2[C@H:15]([NH2:18])[C:16](=[O:17])[N:13]2[C:12]=1[C:21]([OH:23])=[O:22])=O.[Bi](Cl)(Cl)Cl>CO>[NH2:18][CH:15]1[C:16](=[O:17])[N:13]2[C:12]([C:21]([OH:23])=[O:22])=[C:11]([CH2:10][O:9][CH3:7])[CH2:20][S:19][C@H:14]12Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
To 20 ml of carbon tetrachloride were added 2.72 g of 7-ACA, 2.6 g of methanol, 2.7 g of stannic chloride and 15 g of bismuth trichloride. The mixture was heated at 50° C. for 40 min to advance a reaction. After completion of the reaction, the reaction mixture was cooled to 5° C. The resulting precipitate was filtered off. To the filtrate was added 50 ml of water and, then, 0.3 g of activated carbon, and then the mixture was stirred, followed by filtration. The filtrate was adjusted to pH 3.5 with sodium bicarbonate, and concentrated by evaporation under reduced pressure, thereby to form a precipitate. The precipitate was collected by filtration, and washed with 10 ml of cold water and, then, with 10 ml of cold methanol to obtain the desired product, namely 7-amino-3-methoxymethyl-3-cephem-4-carboxylic acid. The amount of the desired product was 1.29 g. The yield of the desired product was 53 %.
Workup
- customa reaction
- customAfter completion of the reaction
- temperaturethe reaction mixture was cooled to 5° C
- filtrationThe resulting precipitate was filtered off
- additionTo the filtrate was added 50 ml of water
- filtrationfollowed by filtration
- concentrationconcentrated by evaporation under reduced pressure
- customto form a precipitate
- filtrationThe precipitate was collected by filtration
- washwashed with 10 ml of cold water
Sources & evidence
- ORD record
- ord-ca66dff528574b3fbfc496251a465f7d
- Source dataset
- uspto-grants-1990_02
- Patent number
- US04902793
Reaction notes
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