Bismuth trichloride → 7-Amino-3-methoxymethyl-3-cephem-4-carboxylic acid
Reaction equation
S1(CCCC1)(=O)=O.C[C:9]([O:11][CH2:12][C:13]1[CH2:22][S:21][C@@H:16]2[C@H:17]([NH2:20])[C:18](=[O:19])[N:15]2[C:14]=1[C:23]([OH:25])=[O:24])=O.[Bi](Cl)(Cl)Cl>CO>[NH2:20][CH:17]1[C:18](=[O:19])[N:15]2[C:14]([C:23]([OH:25])=[O:24])=[C:13]([CH2:12][O:11][CH3:9])[CH2:22][S:21][C@H:16]12Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
To 10 ml of sulfolane were added 2.72 g of 7-ACA, 19 g of bismuth trichloride and 1.1 g of methanol. The mixture was heated at 60° C. for 35 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 30 ml of water while cooling on ice. Then, the filtrate was adjusted to pH 3.5 with sodium bicarbonate at a temperature of from 0° C. to 5° C., thereby to form a white crystalline precipitate. The resulting 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 0.76 g. The yield of the desired product was 31 %.
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 30 ml of water
- temperaturewhile cooling on ice
- customwas adjusted to pH 3.5 with sodium bicarbonate at a temperature of from 0° C. to 5° C.
- customto form a white crystalline precipitate
- filtrationThe resulting precipitate was collected by filtration
- washwashed with 10 ml of cold water
Sources & evidence
- ORD record
- ord-1d2279e77fb841a5968ee875f866c600
- Source dataset
- uspto-grants-1990_02
- Patent number
- US04902793
Reaction notes
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