Dimethylformamide → 7-[2-(2-formamidothiazol-4-yl)-2-cyanomethoxyiminoacetamido]-3-(1-allyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid

HRID 255771Notes

Reaction equation

HRID 255771 reaction equation
[CH:1]([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:13][O:14][CH2:15][C:16](=O)[NH2:17])[C:10]([OH:12])=O)[N:8]=1)=[O:2].CN(C)C=O.P(Cl)(Cl)(Cl)=O.[NH2:29][CH:30]1[C:50](=[O:51])[N:32]2[C:33]([C:47]([OH:49])=[O:48])=[C:34]([CH2:37][S:38][C:39]3[N:43]([CH2:44][CH:45]=[CH2:46])[N:42]=[N:41][N:40]=3)[CH2:35][S:36][C@H:31]12>O1CCCC1.CC(C)=O>[CH:1]([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:13][O:14][CH2:15][C:16]#[N:17])[C:10]([NH:29][CH:30]2[C:50](=[O:51])[N:32]3[C:33]([C:47]([OH:49])=[O:48])=[C:34]([CH2:37][S:38][C:39]4[N:43]([CH2:44][CH:45]=[CH2:46])[N:42]=[N:41][N:40]=4)[CH2:35][S:36][C@H:31]23)=[O:12])[N:8]=1)=[O:2]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 538052302-(2-Formamidothiazol-4-yl)-2-carbamoylmethoxyiminoacetic acidHCID 704326537-amino-3-(1-allyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid

Product 1

HCID 1317152997-[2-(2-formamidothiazol-4-yl)-2-cyanomethoxyiminoacetamido]-3-(1-allyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acidYield 68.2%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-(2-formamidothiazol-4-yl)-2-carbamoylmethoxyiminoacetic acid (syn isomer, 1.5 g.), N,N-dimethylformamide (1.31 g.) and phosphoryl chloride (2.74 g.) in tetrahydrofuran (15 ml.) and a solution of 7-amino-3-(1-allyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid (2.96 g.) in 50% aqueous acetone (30 ml.) were treated in a similar manner to that of Example 9-(1) to give 7-[2-(2-formamidothiazol-4-yl)-2-cyanomethoxyiminoacetamido]-3-(1-allyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid (syn isomer, 2.22 g.).

Sources & evidence

ORD record
ord-67d1c2e6981648f6b59d2080fd11da0c
Source dataset
uspto-grants-1987_10
Patent number
US04698337

Reaction notes

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