85506-30-5

Basic information

• Product Name: trans-2-[[[1-(2-aminothiazol-4-yl)-2-[(2-methyl-4-oxo-1-sulphoazetidin-3-yl)amino]-2-oxoethylidene]amino]oxy]-2-methylpropionic acid
• Synonyms: trans-2-[[[1-(2-aminothiazol-4-yl)-2-[(2-methyl-4-oxo-1-sulphoazetidin-3-yl)amino]-2-oxoethylidene]amino]oxy]-2-methylpropionic acid;trans-2-[[[1-(2-Amino-4-thiazolyl)-2-[(2-methyl-4-oxo-1-sulfo-3-azetidinyl)amino]-2-oxoethylidene]amino]oxy]-2-methylpropanoic acid;Einecs 287-382-4;trans-2-(((1-(2-Aminothiazol-4-yl)-2-((2-methyl-4-oxo-1-sulphoazetidin-3-yl)amino)-2-oxoethylidene)amino)oxy)-2-methylpropionic acid
• CAS NO: 85506-30-5
• Molecular Formula: C13H17N5O8S2
• Molecular Weight: 435.43278
• EINECS: 287-382-4
• Mol File: 85506-30-5.mol
• Article Data: 18

Chemical Properties

• Appearance: /
• Density: 1.83g/cm³
• Refractive Index: 1.74
• PKA: -0.29±0.60(Predicted)
• CAS DataBase Reference: trans-2-[[[1-(2-aminothiazol-4-yl)-2-[(2-methyl-4-oxo-1-sulphoazetidin-3-yl)amino]-2-oxoethylidene]amino]oxy]-2-methylpropionic acid(CAS DataBase Reference)
• NIST Chemistry Reference: trans-2-[[[1-(2-aminothiazol-4-yl)-2-[(2-methyl-4-oxo-1-sulphoazetidin-3-yl)amino]-2-oxoethylidene]amino]oxy]-2-methylpropionic acid(85506-30-5)
• EPA Substance Registry System: trans-2-[[[1-(2-aminothiazol-4-yl)-2-[(2-methyl-4-oxo-1-sulphoazetidin-3-yl)amino]-2-oxoethylidene]amino]oxy]-2-methylpropionic acid(85506-30-5)

Safety Data

• Hazardous Substances Data: 85506-30-5(Hazardous Substances Data)

Usage

InChI:InChI=1/C13H17N5O8S2/c1-5-7(10(20)18(5)28(23,24)25)16-9(19)8(6-4-27-12(14)15-6)17-26-13(2,3)11(21)22/h4-5,7H,1-3H3,(H2,14,15)(H,16,19)(H,21,22)(H,23,24,25)

Upstream product

• 7732-18-5 water 
• 123539-91-3 3-<<(2-amino-4-thiazolyl)-<<1-(diphenylmethoxycarbonyl)-1-methyl ethoxy>-imino>-acetyl>-amino>-4-methyl-2-oxoazetidi-ne-1-sulfonic acid 
• 80082-65-1 (3S-trans)-3-Amino-4-methyl-2-oxo-1-azetidinesulfonic acid 
• 89604-92-2 (Z)-2-<<<1-(2-amino-4-thiazolyl)-2-<(2-benzothiazolyl)thio>-2-oxoethylidene>amino>oxy>-2-methyl propanoic acid 1,1-dimethylethyl ester 
• 78110-38-0 azthreonam 
• 86299-47-0 (Z)-2-(2-aminothiazol-4-yl)-2-(1-tert-butoxycarbonyl-1-methylethoxy)iminoacetic acid 
• 102507-85-7 2-amino-α-[(1-carboxy-1-methylethoxy)imino]-4-thiazoleacetic acid 
• 477528-80-6 2-amino-4-[(1-carboxy-1-methyl-ethoxyimino)-(2,5-dioxo-pyrrolidin-1-yloxycarbonyl)-methyl]-thiazol-3-ium methanesulfonate 
• 139714-28-6 (Z)-2-[[[1-(2-amino-4-thiazolyl)-2-(3-oxido-1H-benzotriazol-1-yl)-2-oxoethylidene]amino]oxy]-2-methylpropanoic acid methanesulfonate (1:1) salt 
• 139714-26-4 (Z)-2-[[[1-(2-amino-4-thiazolyl)-2-(3-oxido-1H-benzotriazol-1-yl)-2-oxoethylidene]amino]oxy]-2-methylpropanoic acid diphenylmethyl ester methanesulfonate (1:1) salt 

Relevant articles and documents

Novel crystal form of compound for treating bacterial infection and preparation method thereof

The invention belongs to the field of medicines, and discloses a new crystal form of a compound for treating bacterial infection and a preparation method thereof. Specifically, the invention discloses a new crystal form of an aztreonam compound and a preparation method thereof. The novel aztreonam crystal form disclosed by the invention is different from the prior art, and an X-ray powder diffraction pattern measured by using Cu-K alpha rays is as shown in Figure 1. According to the invention, the pH value is adjusted in sections after the purified water is added, so that the problem that triethylamine easily exceeds the standard is solved, and meanwhile, the novel aztreonam crystal form with good stability, low solvent residue and low impurity content is prepared and is suitable for industrial mass production.

An improved method for the synthesis of Aztreonam

The invention provides an improved synthetic method of aztreonam. According to the improved synthetic method, alpha-(2-aminothiazole-4-yl)-alpha-[(tert-butoxycarbonyl)-propoxyimino)] acetic acid mercaptobenzothiazole ester, and (2S, 3S) 3-amino-2-methyl-4-oxoazetidine sulfonic acid are taken as reaction intermediates; an organic amine is used as a catalyst; and a mixed acid water solution of formic acid and an organic acid is used for removing tertiary butyl protecting group so as to obtain aztreonam. Separation of the intermediates is not necessary, operation is simple and convenient, deprotection method is mild, yield is high, and product purity is high.

PROCESS FOR MAKING AZTREONAM

A simplified process for the one-pot preparation of aztreonam, using azetidine and TAEM as starting materials, without the intermediary separation of t-butyl-aztreonam is provided.