2-Mercaptobenzothiazolyl-(Z)-(2-aminothiazol-4-yl)-2-(tert-butoxycarbonyl) isopropoxyiminoacetate

Base Information

• Chemical Name: 2-Mercaptobenzothiazolyl-(Z)-(2-aminothiazol-4-yl)-2-(tert-butoxycarbonyl) isopropoxyiminoacetate
• CAS No.: 89604-92-2
• Molecular Formula: C20H22N4O4S3
• Molecular Weight: 478.617
• European Community (EC) Number: 419-040-9
• DSSTox Substance ID: DTXSID301104852
• Nikkaji Number: J3.229.370K
• Wikidata: Q76423270
• Mol file: 89604-92-2.mol

Synonyms:taem;89604-92-2;158183-05-2;2-Mercaptobenzothiazolyl;(Z)-tert-Butyl 2-(((1-(2-aminothiazol-4-yl)-2-(benzo[d]thiazol-2-ylthio)-2-oxoethylidene)amino)oxy)-2-methylpropanoate;2-Mercaptobenzothiazolyl-(Z)-(2-aminothiazol-4-yl)-2-(tert-butoxycarbonyl) isopropoxyiminoacetate;(E)-tert-butyl 2-(1-(2-aminothiazol-4-yl)-2-(benzo[d]thiazol-2-ylthio)-2-oxoethylideneaminooxy)-2-methylpropanoate;tert-butyl 2-[(Z)-[1-(2-amino-1,3-thiazol-4-yl)-2-(1,3-benzothiazol-2-ylsulfanyl)-2-oxoethylidene]amino]oxy-2-methylpropanoate;MFCD00071548;TERT-BUTYL 2-{[(Z)-[1-(2-AMINO-1,3-THIAZOL-4-YL)-2-(1,3-BENZOTHIAZOL-2-YLSULFANYL)-2-OXOETHYLIDENE]AMINO]OXY}-2-METHYLPROPANOATE;EC 419-040-9;SCHEMBL4727203;DTXSID301104852;2-mercaptobenzothiazolyl (z)-2-(2-aminothiazol-4-yl)-2-(2-t-butoxycarbonylprop-2-oxyimino) acetate;AKOS015920134;AC-5571;CS-W019525;GS-3101;benzothiazol-2-yl-(z)-2-(tert-butoxycarbonylprop-2-oxyimino)-2-(2-aminothiazol-4-yl)thi-oacetate;S-2-Benzothiazoyl-(Z)-2-(1-tert-butoxycanbonyl-1-methylethoxyimino)-(2-amino-thiazol-4-yl) acetate;O10235;J-509777;2-mercaptobenzolyl-(2-aminothiazol-4-yl)-[(tert-butoxycarbonyl)isopropoxyimino]acetate;s-2-benzothiazolyl-(2)-2-(1-terbatoxycanbonyl-1-methylethoxyimino)-4-thiazole acetate;(Z)-2-[(2-Aminothiazol-4-yl)-(benzothiazol-2-yloxythiocarbonyl)-methyleneaminooxy]-2-methyl-propionic acid t-butyl ester;(z)-tert-butyl 2-(1-(2-aminothiazol-4-yl)-2-(benzo[d]thiazol-2-ylthio)-2-oxoethylideneaminooxy)-2-me;1,1-Dimethylethyl 2-[[(Z)-[1-(2-amino-4-thiazolyl)-2-(2-benzothiazolylthio)-2-oxoethylidene]amino]oxy]-2-methylpropanoate;2-[[(Z)-[1-(2-Amino-4-thiazolyl)-2-(2-benzothiazolylthio)-2-oxoethylidene]amino]oxy]-2-methylpropanoic Acid 1,1-Dimethylethyl Ester;2-mercaptobenzothiazolyl-(z)(2-aminothiazole-4yl)-2-(tert-butoxycarbonyl)isopropoxyimino acetate;2-Mercaptobenzoyl-alpha-(2-aminothiazol-4-yl)-alpha-[(tert-butoxycarbonyl)]isopropoxyimino]acetate;benzothiazol-2-yl-(z)-2-(tert-butoxycarbonylprop-2-oxyimino)-(2-aminothiazol-4-yl) thioacetate;benzothiazol-2-yl-(z)-2-(tert-butoxycarbonylprop-2-oxyimino)-(2-aminothiazol-4-yl)thioacetate 89604-;s-2-benzothiazolyl (z)-2-(2-aminothiazol-4-yl)-2-(1-t-butoxycarbonyl-1-methyl)ethoxyiminothioacetate;s-2-benzothiazoyl-(z)-2-(1-tert-butoxycarbonyl-1-methylethoxyimino)-(2-amino-thiazol-4-yl) acetate;s-2-benzothiazoyl-(z)-2-(1-tert-butoxycarbonyl-1-methylethoxyimino)-2-(aminothiazol-4-yl)acetate;tert-Butyl 2-(((1-(2-aminothiazol-4-yl)-2-(benzo[d]thiazol-2-ylthio)-2-oxoethylidene)amino)oxy)-2-methylpropanoate

Chemical Property of 2-Mercaptobenzothiazolyl-(Z)-(2-aminothiazol-4-yl)-2-(tert-butoxycarbonyl) isopropoxyiminoacetate

Chemical Property:

• Vapor Pressure: 2.26E-15mmHg at 25°C
• Melting Point: 138-140 °C
• Refractive Index: 1.671
• Boiling Point: 621.6 °C at 760 mmHg
• PKA: 0.83±0.10(Predicted)
• Flash Point: 329.7 °C
• PSA: 198.54000
• Density: 1.41 g/cm³
• LogP: 5.07610
• Storage Temp.: Hygroscopic, -20?C Freezer, Under Inert Atmosphere
• Solubility.: Chloroform, Methanol
• XLogP3: 5.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 9
• Exact Mass: 478.08031872
• Heavy Atom Count: 31
• Complexity: 713

Purity/Quality:

99.9% ^*data from raw suppliers

2-Mercaptobenzothiazolyl-(Z)-(2-aminothiazol-4-yl)-2-(tert-butoxycarbonyl)isopropoxyiminoacetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): R53:
• Hazard Codes: R53:
• Statements: 53
• Safety Statements: 61

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)C(C)(C)ON=C(C1=CSC(=N1)N)C(=O)SC2=NC3=CC=CC=C3S2
• Isomeric SMILES: CC(C)(C)OC(=O)C(C)(C)O/N=C(/C1=CSC(=N1)N)\C(=O)SC2=NC3=CC=CC=C3S2
• Uses: An intermediate for the preparation of cephalosporin derivatives.

Technology Process of 2-Mercaptobenzothiazolyl-(Z)-(2-aminothiazol-4-yl)-2-(tert-butoxycarbonyl) isopropoxyiminoacetate

There total 3 articles about 2-Mercaptobenzothiazolyl-(Z)-(2-aminothiazol-4-yl)-2-(tert-butoxycarbonyl) isopropoxyiminoacetate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.5%

di(benzothiazol-2-yl)disulfide (120-78-5) + (Z)-2-(2-aminothiazol-4-yl)-2-(1-tert-butoxycarbonyl-1-methylethoxy)iminoacetic acid (86299-47-0) → 2-benzothiazolyl 2-(2-aminothiazol-4-yl)-2-<<1-(tert-butoxycarbonyl)-1-methylethoxy>imino>thioacetate (89604-92-2,158183-05-2)

Guidance literature:

With pyridine; N,N-dimethyl-aniline; triethyl phosphite; In acetonitrile; benzene; at 18 - 25 ℃; for 0.5h; Reagent/catalyst; Microwave irradiation; Green chemistry;

Reference yield: 92.6%

di(benzothiazol-2-yl)disulfide (120-78-5) + (Z)-2-(2-aminothiazol-4-yl)-2-(1-tert-butoxycarbonyl-1-methylethoxy)iminoacetic acid (86299-47-0) → (Z)-2-<<<1-(2-amino-4-thiazolyl)-2-<(2-benzothiazolyl)thio>-2-oxoethylidene>amino>oxy>-2-methyl propanoic acid 1,1-dimethylethyl ester (89604-92-2,158183-05-2)

Guidance literature:

di(benzothiazol-2-yl)disulfide; (Z)-2-(2-aminothiazol-4-yl)-2-(1-tert-butoxycarbonyl-1-methylethoxy)iminoacetic acid; With pyridine; triethylamine; In acetonitrile; at 21 - 30 ℃; for 0.833333h;

With triethyl phosphite; In acetonitrile; at 21 ℃; for 5.5h; Temperature;

Reference yield: 92.4%

di(benzothiazol-2-yl)disulfide (120-78-5) + (Z)-2-(2-aminothiazol-4-yl)-2-(1-tert-butoxycarbonyl-1-methylethoxy)iminoacetic acid (86299-47-0) → (Z)-2-<<<1-(2-amino-4-thiazolyl)-2-<(2-benzothiazolyl)thio>-2-oxoethylidene>amino>oxy>-2-methyl propanoic acid 1,1-dimethylethyl ester (89604-92-2,158183-05-2) + 2-Mercaptobenzothiazole (149-30-4,118090-09-8)

Guidance literature:

di(benzothiazol-2-yl)disulfide; (Z)-2-(2-aminothiazol-4-yl)-2-(1-tert-butoxycarbonyl-1-methylethoxy)iminoacetic acid; With pyridine; In acetonitrile; at 25 ℃; for 0.5h; Inert atmosphere;

With phosphorous acid trimethyl ester; In acetonitrile; at 25 ℃; for 7h; Inert atmosphere;

DOI:10.1007/s11164-012-0583-0

upstream raw materials:

di(benzothiazol-2-yl)disulfide

(Z)-2-(2-aminothiazol-4-yl)-2-(1-tert-butoxycarbonyl-1-methylethoxy)iminoacetic acid

Downstream raw materials:

diphenylmethyl 7-<2-(2-aminothiazol-4-yl)-2-<<(Z)-1-(tert-butoxycarbonyl)-1-methylethoxy>imino>acetamido>-3-<<(3,4-diacetoxybenzoyl)oxy>methyl>ceph-3-em-4-carboxylate

diphenylmethyl 7-<2-(2-aminothiazol-4-yl)-2-<<(Z)-1-(tert-butoxycarbonyl)-1-methylethoxy>imino>acetamido>-3-<<(3-bromo-4,5-diacetoxybenzoyl)oxy>methyl>ceph-3-em-4-carboxylate

7-<2-(aminothiazol-4-yl)-2-<(Z)-(1-carboxy-1-methylethoxy)imino>acetamido>-3-<2-(3-bromo-4,5-dihydroxyphenyl)ethenyl>ceph-3-em-4-carboxylic acid

7-<2-(aminothiazol-4-yl)-2-<(Z)-(1-carboxy-1-methylethoxy)imino>acetamido>-3-<2-(3-bromo-4,5-dihydroxyphenyl)ethenyl>ceph-3-em-4-carboxylic acid

Refernces

• 1、 -. "Method for synthesizing 2-Mercaptobenzothiazolyl-(Z)-(2-aminothiazol-4-yl)-2-(tert-butoxycarbonyl) isopropoxyiminoacetate". Paragraph 0028-0033. . Retrieved 2017/07/21.
• 2、 Li, Lei,Wang, Guangyuan,Wei, Shanshan,Yan, Xilong,Chen, Ligong. "A modified procedure for synthesis of the side chain of ceftazidime-activated thioester". . p. 615 - 620. Retrieved 2013/07/27.