Methyl iodide → HCID 70616771, compound

HRID 1679696Notes

Reaction equation

HRID 1679696 reaction equation
[C:1]1([CH2:7][C:8]([NH:10][CH:11]2[C:33](=[O:34])[N:13]3[C:14]([C:20]([O:22][CH2:23][C:24]4[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[CH:26][CH:25]=4)=[O:21])=[C:15]([Cl:19])[CH2:16][S:17](=[O:18])[C@H:12]23)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[CH3:37]I>CN(C)C=O.O.C(OCC)(=O)C>[C:1]1([CH2:7][C:8]([NH:10][CH:11]2[C:33](=[O:34])[N:13]3[C:14]([C:20]([O:22][CH2:23][C:24]4[CH:25]=[CH:26][C:27]([N+:30]([O-:32])=[O:31])=[CH:28][CH:29]=4)=[O:21])=[C:15]([Cl:19])[CH:16]([CH3:37])[S:17](=[O:18])[C@H:12]23)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 70617090HCID 70617090, compound

Product 1

HCID 70616771HCID 70616771, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of p-nitrobenzyl 7-phenylacetamido-3-chloro-3-cephem-4-carboxylate-1-oxide (504 mg) in dimethylformamide (20 ml) one adds a 50% suspension of sodium hydride (48 mg) in mineral oil under nitrogen atmosphere, stirs for 40 minutes, adds methyl iodide (0.5 ml), stirs for 15 minutes at room temperature, dilutes with water, extracts with ethyl acetate, washes with water, dries, concentrates under reduced pressure, and purifies by chromatography to give p-nitrobenzyl 7-phenylacetamido-2-methyl-3-chloro-3-cephem-4-carboxylate-1-oxide (38 mg).

Workup

  1. waitstirs for 15 minutes at room temperature

Sources & evidence

ORD record
ord-aa6f0a822e5c42e7848b7dadccf1fb45
Source dataset
uspto-grants-1978_03
Patent number
US04081595

Reaction notes

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