Acetone → Amoxicillin

HRID 1855929Notes

Reaction equation

[CH3:1][C:2]1([CH3:27])[S:6][C@@H:5]2[C@H:7]([N:10]3C(C)(C)[NH:14][C@H:13]([C:18]4[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=4)[C:11]3=[O:12])[C:8](=[O:9])[N:4]2[C@H:3]1[C:24]([OH:26])=[O:25].CC(C)=[O:30]>>[CH3:27][C:2]1([CH3:1])[S:6][C@@H:5]2[C@H:7]([NH:10][C:11]([C@H:13]([NH2:14])[C:18]3[CH:23]=[CH:22][C:21]([OH:30])=[CH:20][CH:19]=3)=[O:12])[C:8](=[O:9])[N:4]2[C@H:3]1[C:24]([OH:26])=[O:25]

Participants

Reactant 2

HCID 180Acetone

HCID 443387Hetacillin

Product 1

HCID 33613Amoxicillin

Procedure

The procedure of Example 1 was repeated with the substitution for the hetacillin therein of an equimolar weight of heta-amoxicillin (also called p-hydroxyhetacillin or the acetone adduct of amoxicillin) to produce the title compound. The product appeared by NMR to be 85-90% pure with respect to the acetone adduct group.

Sources & evidence

ORD record: ord-6c3258fcb26c42059ea8089dfb5becaf
Source dataset: uspto-grants-1980_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04217274

Reaction notes

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