Phosphoric Acid → Penicillin G

HRID 1992243Notes

Reaction equation

HRID 1992243 reaction equation
CC(O)COC.CC1(C)S[C@@H]2[C@H](N)C(=O)N2[C@H]1C(O)=O.[CH3:21][C:22]1([CH3:44])[S:26][C@@H:25]2[C@H:27]([NH:30][C:31]([C@H:33](N)[C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=3)=[O:32])[C:28](=[O:29])[N:24]2[C@H:23]1[C:41]([OH:43])=[O:42].S([O-])(OCCCCCCCCCCCC)(=O)=O.[Na+].OP(O)(O)=O.[OH-].[Na+]>C(#N)C>[CH3:21][C:22]1([CH3:44])[S:26][C@@H:25]2[C@H:27]([NH:30][C:31]([CH2:33][C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=3)=[O:32])[C:28](=[O:29])[N:24]2[C@H:23]1[C:41]([OH:43])=[O:42]

Participants

8

Reactant 6

HCID 1004Phosphoric AcidHCID 6249AmpicillinHCID 79001-Methoxy-2-propanolHCID 110826-Aminopenicillanic acidHCID 14798Sodium HydroxideHCID 3423265Sodium Lauryl Sulfate

Product 1

HCID 5904Penicillin G

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Analisys: Concentrations of PGME, 6-APA, ampicillin and PG using HPLC. Column Waters C18: Nova-Pak, 60 Å, diameter 4 μm, 3.9×150 mm. Mobile phase: 35% acetonitrile, 2‰ SDS (sodium dodecyl sulfate), 10 mM H3PO4, 5 mM K2H2PO4, pH 4.6 and 25° C., 225 nm, flow 1 mL/min. Synthesis experiments: 25° C., pH 6.5 controlled by automatic addition of NaOH. Jacketed glass vortex flow reactor, internal cylinder of stainless steel 316. Reaction volume, 50 mL. Reactor internal diameter, 36 mm. Rotary cylinder diameter, 10 mm (radius ratio 0.28). Volume of biocatalyst, 20 mL. Enzymatic load, 10 IU/(mL of reactor).

Workup

  1. customSynthesis experiments
  2. customReaction volume, 50 mL

Sources & evidence

ORD record
ord-21741b5378c245d180a653c4cf89bc60
Source dataset
uspto-grants-2010_01
Patent number
US07648831B2

Reaction notes

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