Phosphorus oxychloride → 7-[2-(2-Aminothiazole-4-yl)-2-n-hexyloxyiminoacetamido]-3-cephem-4-carboxylic acid

HRID 1905252Notes

Reaction equation

HRID 1905252 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:11][O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[C:8]([OH:10])=O)[N:6]=1.P(Cl)(Cl)(Cl)=O.C[Si](CC(N)=O)(C)C.[NH2:32][CH:33]1[C:43](=[O:44])[N:35]2[C:36]([C:40]([OH:42])=[O:41])=[CH:37][CH2:38][S:39][C@H:34]12>O1CCCC1.CN(C)C=O.O>[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:11][O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[C:8]([NH:32][CH:33]2[C:43](=[O:44])[N:35]3[C:36]([C:40]([OH:42])=[O:41])=[CH:37][CH2:38][S:39][C@H:34]23)=[O:10])[N:6]=1

Participants

8

Reactant 4

HCID 24813Phosphorus oxychlorideHCID 357676Acetamide, 2-(trimethylsilyl)-HCID 12941984(6R)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acidHCID 540705992-(2-Aminothiazol-4-yl)-2-n-hexyloxyiminoacetic acid

Product 1

HCID 1317124707-[2-(2-Aminothiazole-4-yl)-2-n-hexyloxyiminoacetamido]-3-cephem-4-carboxylic acidYield 24.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

2-(2-Aminothiazol-4-yl)-2-n-hexyloxyiminoacetic acid (syn isomer, 3 g.), water (0.15 g.), phosphoryl chloride (3.8 g.), trimethylsilyl-acetamide (10.7 g.), N,N-dimethylformamide (1.0 g.), tetrahydrofuran (50 ml.) and 7-amino-3-cephem-4-carboxylic acid (2.0 g.) were treated in a similar manner to that of Example 18 to give 7-[2-(2-aminothiazol-4-yl)-2-n-hexyloxyiminoacetamido]-3-cephem-4-carboxylic acid (syn isomer, 1.1 g.).

Sources & evidence

ORD record
ord-eeaef16f22f24eea95620c79e99503eb
Source dataset
uspto-grants-1989_06
Patent number
US04841062

Reaction notes

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