Phenylacetyl chloride → p-Nitrobenzyl 7-phenylacetamido-3-chloro-3-cephem-4-carboxylate

HRID 443530Notes

Reaction equation

HRID 443530 reaction equation
[NH2:1][CH:2]1[C:23](=[O:24])[N:4]2[C:5]([C:10]([O:12][CH2:13][C:14]3[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=3)=[O:11])=[C:6]([Cl:9])[CH2:7][S:8][C@H:3]12.[C:25]1([CH2:31][C:32](Cl)=[O:33])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(=O)(O)[O-].[Na+]>CC(C)=O>[C:25]1([CH2:31][C:32]([NH:1][CH:2]2[C:23](=[O:24])[N:4]3[C:5]([C:10]([O:12][CH2:13][C:14]4[CH:15]=[CH:16][C:17]([N+:20]([O-:22])=[O:21])=[CH:18][CH:19]=4)=[O:11])=[C:6]([Cl:9])[CH2:7][S:8][C@H:3]23)=[O:33])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 7679Phenylacetyl chlorideHCID 516892Sodium BicarbonateHCID 676435564-Nitrobenzyl 7-amino-3-chloro-3-cephem-4-carboxylate

Product 1

HCID 67655773p-Nitrobenzyl 7-phenylacetamido-3-chloro-3-cephem-4-carboxylate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

For example, p-nitrobenzyl 7-amino-3-chloro-3-cephem-4-carboxylate is reacted with phenylacetyl chloride in cold aqueous acetone containing sodium bicarbonate to provide p-nitrobenzyl 7-phenylacetamido-3-chloro-3-cephem-4-carboxylate.

Sources & evidence

ORD record
ord-146f78c3c7994e5ab59a567c911fdce6
Source dataset
uspto-grants-1981_04
Patent number
US04260745

Reaction notes

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