Phosphorus trichloride → 4-Nitrobenzyl 7-[2-(2-thienyl)acetamido]-3-chloro-3-cephem-4-carboxylate

HRID 1439794Notes

Reaction equation

HRID 1439794 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([NH:9][CH:10]1[C:31](=[O:32])[N:12]2[C:13]([C:18]([O:20][CH2:21][C:22]3[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][CH:23]=3)=[O:19])=[C:14](O)[CH2:15][S:16][C@H:11]12)=[O:8].P(Cl)(Cl)[Cl:34]>CN(C=O)C>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([NH:9][CH:10]1[C:31](=[O:32])[N:12]2[C:13]([C:18]([O:20][CH2:21][C:22]3[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][CH:23]=3)=[O:19])=[C:14]([Cl:34])[CH2:15][S:16][C@H:11]12)=[O:8]

Participants

4

Reactant 2

HCID 24387Phosphorus trichlorideHCID 70559815p-Nitrobenzyl 7-[2-(2-thienyl)acetamido]-3-hydroxy-3-cephem-4-carboxylate

Product 1

HCID 705589584-Nitrobenzyl 7-[2-(2-thienyl)acetamido]-3-chloro-3-cephem-4-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Alternatively, the 3-hydroxy-3-cephem esters prepared via the reduction of a sulfoxide compound of the formula I can be reacted with phosphorus trichloride is DMF to effect chlorination of the 3-hydroxy group and provide a 3-chloro-3-cephem ester. For example, 4-nitrobenzyl 7-[2-(2-thienyl)acetamido]-3-hydroxy-3-cephem-4-carboxylate is reacted with phosphorus trichloride in DMF to yield 4-nitrobenzyl 7-[2-(2-thienyl)acetamido]-3-chloro-3-cephem-4-carboxylate. Cleavage of the 4-nitrobenzyl ester group provides the antibiotic compound 7-[2-(2-thienyl)acetamido]-3-chloro-3-cephem-4-carboxylic acid. These 3-halo-3-cephem antibiotics are likewise fully disclosed in my copending applications Ser. Nos. 457,150 and 457,153 filed Apr. 1, 1974 the latter now U.S. Pat. No. 3,925,372 issued Dec. 9, 1975.

Sources & evidence

ORD record
ord-5e4074cb0d2c4265ad0fdf2f5444fbee
Source dataset
uspto-grants-1977_11
Patent number
US04060688

Reaction notes

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