Phenylacetyl chloride → HCID 131710523, compound

HRID 1730301Notes

Reaction equation

HRID 1730301 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)=[S:11])=[C:6]([CH3:9])[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)=[S:11])=[C:6]([CH3:9])[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 131710524HCID 131710524, compound

Product 1

HCID 131710523HCID 131710523, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

For example, p-nitrobenzyl 7-amino-3-methylthio-3-cephem-4-carboxylate is reacted with phenylacetyl chloride in cold aqueous acetone containing an excess of sodium bicarbonate to provide the acylated compound p-nitrobenzyl 7-phenylacetamido-3-methylthio-3-cephem-4-carboxylate. Similarly, diphenylmethyl 7-amino-3-(1-methyl-1H-tetrazole-5-ylthio)-3-cephem-4-carboxylate is reacted with 2-thienylacetyl chloride in aqueous acetone at a temperature of about 5° to about 10° C. in the presence of sodium bicarbonate to provide the 7-[2-(2-thienyl)acetamido]ester.

Sources & evidence

ORD record
ord-c2a9b1e1378748819858c5bc4cf25bf1
Source dataset
uspto-grants-1976_11
Patent number
US03992377

Reaction notes

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