2,6-Lutidine → HCID 131715366, compound

HRID 256451Notes

Reaction equation

HRID 256451 reaction equation
Cl.[NH2:2][CH:3]1[C:25](=[O:26])[N:5]2[C:6]([C:12]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=3)=[O:13])=[CH:7][CH:8]([O:10][CH3:11])[S:9][C@H:4]12.C[Si](CC(N)=O)(C)C.N1C(C)=CC=CC=1C.P(Cl)(Cl)(Cl)=O.[CH:48]([NH:50][C:51]1[S:52][C:53]([Br:63])=[C:54]([C:56](=[N:60][O:61][CH3:62])[C:57](O)=[O:58])[N:55]=1)=[O:49]>C(OCC)(=O)C.CN(C)C=O>[CH:48]([NH:50][C:51]1[S:52][C:53]([Br:63])=[C:54]([C:56](=[N:60][O:61][CH3:62])[C:57]([NH:2][CH:3]2[C:25](=[O:26])[N:5]3[C:6]([C:12]([O:14][CH2:15][C:16]4[CH:17]=[CH:18][C:19]([N+:22]([O-:24])=[O:23])=[CH:20][CH:21]=4)=[O:13])=[CH:7][CH:8]([O:10][CH3:11])[S:9][C@H:4]23)=[O:58])[N:55]=1)=[O:49]

Participants

8

Reactant 5

HCID 79372,6-LutidineHCID 24813Phosphorus oxychlorideHCID 357676Acetamide, 2-(trimethylsilyl)-HCID 538011022-(2-Formamido-5-bromothiazol-4-yl)-2-methoxyiminoacetic acidHCID 70418103HCID 70418103, compound

Product 1

HCID 131715366HCID 131715366, compoundYield 88.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of 4-nitrobenzyl 7-amino-2-methoxy-3-cephem-4-carboxylate hydrochloride (2.0 g.), trimethylsilylacetamide (2.0 g.) and 2,6-lutidine (0.58 ml.) in dry ethyl acetate (60 ml.) and a solution of dimethylformamide (0.51 ml.), phosphoryl chloride (0.60 ml.) and 2-(2-formamido-5-bromothiazol-4-yl)-2-methoxyiminoacetic acid (syn isomer, 1.7 g.) in dry ethyl acetate (11.7 ml.) were treated in a similar manner to that of Example 1-(1) to give 4-nitrobenzyl 7-[2-(2-formamido-5-bromothiazol-4-yl)-2-methoxyiminoacetamido]-2-methoxy-3-cephem-4-carboxylate (syn isomer, 2.9 g.).

Sources & evidence

ORD record
ord-73354f26b7cb4022965433d1c6271ec2
Source dataset
uspto-grants-1987_10
Patent number
US04703046

Reaction notes

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