Phosphorus trichloride → HCID 6347548, compound

HRID 443541Notes

Reaction equation

[O:1]([CH2:8][C:9]([NH:11][CH:12]1[C:33](=[O:34])[N:14]2[C:15]([C:20]([O:22]CC3C=CC([N+]([O-])=O)=CC=3)=[O:21])=[C:16]([Cl:19])[CH2:17][S:18][C@H:13]12)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P(Cl)(Cl)Cl>>[O:1]([CH2:8][C:9]([NH:11][CH:12]1[C:33](=[O:34])[N:14]2[C:15]([C:20]([OH:22])=[O:21])=[C:16]([Cl:19])[CH2:17][S:18][C@H:13]12)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Reactant 2

HCID 24387Phosphorus trichloride

HCID 67655752HCID 67655752, compound

Product 1

HCID 6347548HCID 6347548, compound

Procedure

Following the chlorination procedure of Example 19 p-nitrobenzyl 7-phenoxyacetamido-3-chloro-3-cephem-4-carboxylate was prepared with phosphorus trichloride. The p-nitrobenzyl ester group was removed by the acidic hydrogenolysis procedure described by Example 18 to provide the 3-chlorocephalosporanic acid antibiotic compound.

Workup

customThe p-nitrobenzyl ester group was removed by the acidic hydrogenolysis procedure
customto provide the 3-chlorocephalosporanic acid antibiotic compound

Sources & evidence

ORD record: ord-2e6457ebdf3449c8bca543f9ae18040d
Source dataset: uspto-grants-1981_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04260745

Reaction notes

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