Ampicillin → Cephradine

HRID 1650928Notes

Reaction equation

C1C=CC([C@@H](N)C(O)=O)=CC=1.[CH3:12][C:13]1([CH3:36])[S:17][C@@H:16]2[C@H:18]([NH:21][C:22]([C@H:24]([NH2:32])[C:25]3[CH:26]=[CH:27][C:28](O)=[CH:29][CH:30]=3)=[O:23])[C:19](=[O:20])[N:15]2[C@H:14]1[C:33]([OH:35])=[O:34].CC1(C)S[C@@H]2[C@H](NC([C@H](N)C3C=CC=CC=3)=O)C(=O)N2[C@H]1C(O)=O.CC(OCC1CS[C@@H]2[C@H](N)C(=O)N2C=1C(O)=O)=O>>[CH3:36][C:13]1[CH2:12][S:17][C@@H:16]2[C@H:18]([NH:21][C:22]([C@H:24]([NH2:32])[C:25]3[CH2:26][CH:27]=[CH:28][CH2:29][CH:30]=3)=[O:23])[C:19](=[O:20])[N:15]2[C:14]=1[C:33]([OH:35])=[O:34]

Participants

Reactant 4

HCID 6249Ampicillin

HCID 33613Amoxicillin

HCID 70134Phenylglycine, D-

HCID 4413287-Aminocephalosporanic acid

Product 1

HCID 38103Cephradine

Procedure

As an example, D-(-)-(4-hydroxyphenyl)-glycine and D-(-)-phenylglycine are key intermediates in the industrial synthesis of amoxycillin and ampicillin respectively; while D-(-)-2-amino-2-(1,4-cylcohexadien-1-yl)acetic acid may be conveniently be employed in the acylation of 7-amino-cephalosporanic acid to give cefradin.

Sources & evidence

ORD record: ord-4789e74a0b4d4e25b7586dfdb24dd946
Source dataset: uspto-grants-1990_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04925978

Reaction notes

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