Penicillin G → HCID 15670703, compound

HRID 345630Notes

Reaction equation

C(O)(=O)C(O)=O.[NH2:7][CH:8]1[C:11](=[O:12])[N:10]([CH2:13][C:14]([O:16][CH3:17])=[O:15])[CH:9]1[CH2:18][CH2:19][C:20]1[O:21][CH:22]=[CH:23][CH:24]=1.[C:25]1([CH2:31][C:32](OC)=[O:33])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].CC1(C)S[C@@H]2[C@H](NC(CC3C=CC=CC=3)=O)C(=O)N2[C@H]1C(O)=O>O>[C:25]1([CH2:31][C:32]([NH:7][C@@H:8]2[C:11](=[O:12])[N:10]([CH2:13][C:14]([O:16][CH3:17])=[O:15])[C@@H:9]2[CH2:18][CH2:19][C:20]2[O:21][CH:22]=[CH:23][CH:24]=2)=[O:33])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

Conditions

Temperature: 28 °C

Procedure

A 100 mg sample of cis(racemic at 2 and 3 position) 3-amino-2-[2-(2-furanyl)ethyl]-4-oxo-1-azetidine acetic acid, methyl ester oxalate and 121 mg of methyl phenylacetate was added to 0.1 M potassium phosphate buffer(100ml) at pH=6.0, and the temperature maintained at 28° C. Milli-Q™ H2O washed Sclavo penicillin G amidase (0.035 I.U./%mole of substrate; 0.100 I.U./mg of substrate) was added and the reaction allowed to proceed overnight. The reaction mixture was then extracted two times with ethyl acetate and dried over anhydrous sodium sulfate. The ethyl acetate portion was evaporated to dryness in vacuo and the residue was purified by column chromatography using a Kiesegel 60™ column eluted with toluene/ethyl acetate (50/50), to obtain 45.7 mg (42.2% yield) of the title compound.

Workup

extractionThe reaction mixture was then extracted two times with ethyl acetate
dry with materialdried over anhydrous sodium sulfate
customThe ethyl acetate portion was evaporated to dryness in vacuo
customthe residue was purified by column chromatography
washeluted with toluene/ethyl acetate (50/50)

Sources & evidence

ORD record: ord-685a014d39a442f0bdbb97ca1f420884
Source dataset: uspto-grants-1991_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05057607

Reaction notes

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