Sodium Bicarbonate → Penicillin G

HRID 364869Notes

Reaction equation

HRID 364869 reaction equation
[CH3:1][C:2]1([CH3:23])[S:6][C@@H:5]2[C@H:7]([NH:10][C:11]([CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[O:12])[C:8](=[O:9])[N:4]2[C@H:3]1[C:20]([O-:22])=[O:21].[K+].C(=O)(O)[O-].[Na+]>O1CCOCC1>[CH3:1][C:2]1([CH3:23])[S:6][C@@H:5]2[C@H:7]([NH:10][C:11]([CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[O:12])[C:8](=[O:9])[N:4]2[C@H:3]1[C:20]([OH:22])=[O:21]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 23664709Penicillin G Potassium

Product 1

HCID 5904Penicillin G

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Reaction of potassium benzylpenicillin with α-chlorodiethylcarbonate in an aqueous solution of 70% dioxane in the presence of sodium bicarbonate. The 1-ethoxycarbonyloxyethyl ester of benzylpenicillin which is obtained is subjected to the reaction of removing the phenylacetic chain, via the iminochloride-iminoether, in order to obtain the 1-ethoxycarbonyloxyethyl ester of the 6-aminopenicillanic acid, which is isolated as the hydrochloride.

Sources & evidence

ORD record
ord-af4a2827f5f748b0a629fde2a64f9044
Source dataset
uspto-grants-1986_08
Patent number
US04606865

Reaction notes

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