Hydrochloric Acid → 6-Aminopenicillanic acid
Reaction equation
[CH3:1][C:2]1([CH3:23])[S:6][C@@H:5]2[C@H:7]([NH:10]C(CC3C=CC=CC=3)=O)[C:8](=[O:9])[N:4]2[C@H:3]1[C:20]([O-:22])=[O:21].[K+].Cl>>[CH3:1][C:2]1([CH3:23])[S:6][C@@H:5]2[C@H:7]([NH2:10])[C:8](=[O:9])[N:4]2[C@H:3]1[C:20]([OH:22])=[O:21]Participants
Procedure
120 ml of the immobilized preparation of Escherichia coli ATCC 9637 are charged into a 2.1 cm × 34.8 cm column. 500 ml of an aqueous 1 % potassium Penicillin G solution (pH 9.0) are passed through the column at 40°C at the flow rate of 16 ml/hr. The effluent tus obtained is adjusted to pH 2.0 with 2N-hydrochloric acid and washed twice with 10 ml of methylisobutylketone to remove phenylacetic acid. The aqueous layer is again adjusted to pH 7.0 with 2N-sodium hydroxide. Then, the aqueous layer is concentrated at 50°C under reduced pressure to bring its total volume to 5 ml. After adjusting to pH 4.3 with 2N-hydrochloric acid, the concentrated solution is allowed to stand at 27°C overnight. The crystalline precipitate is collected by filtration and dried at 50°C under reduced pressure. 2.23 g of 6-APA are obtained. Yield: 85 % M.p. 204° - 207°C (decomp.)
Workup
- custom120 ml of the immobilized preparation of Escherichia coli ATCC 9637
- additionare charged into a 2.1 cm × 34.8 cm column
- customare passed through the column at 40°C at the flow rate of 16 ml/hr
- customThe effluent tus obtained
- washwashed twice with 10 ml of methylisobutylketone
- customto remove phenylacetic acid
- concentrationThen, the aqueous layer is concentrated at 50°C under reduced pressure
- filtrationThe crystalline precipitate is collected by filtration
- customdried at 50°C under reduced pressure
Sources & evidence
- ORD record
- ord-a6074ca9605f4da681f5f40eeced91e8
- Source dataset
- uspto-grants-1976_04
- Patent number
- US03953291
Reaction notes
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