Phosgene → Cephalosporanic Acid

HRID 1730869Notes

Reaction equation

[CH3:1][C:2]([O:4][CH2:5][C:6]1[CH2:15][S:14][C@@H:9]2[C@H:10](N)[C:11](=[O:12])[N:8]2[C:7]=1[C:16]([OH:18])=[O:17])=[O:3].C(Cl)(Cl)=O.C(Cl)(Cl)=S>>[CH3:1][C:2]([O:4][CH2:5][C:6]1[CH2:15][S:14][C@@H:9]2[CH2:10][C:11](=[O:12])[N:8]2[C:7]=1[C:16]([OH:18])=[O:17])=[O:3]

Participants

Reactant 3

HCID 6371Phosgene

HCID 10040Thiophosgene

HCID 4413287-Aminocephalosporanic acid

Product 1

HCID 12302722Cephalosporanic Acid

Procedure

reaction of 7-ACA with phosgene (or thiophosgene) to yield isocyanato (or isothiocyanato) cephalosporanic acid which is reacted with the appropriate amine of formula R1NH2 and then either catalytic hydrogenation of the 3-acetoxy group to yield the 3-methyl group or displacement of the 3-acetoxy group of 7-ACA with the desired mercaptoheterocyclic compound.

Sources & evidence

ORD record: ord-052e63a9188e46379820f728b856f9a5
Source dataset: uspto-grants-1976_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03994887

Reaction notes

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