(Z)-2-(2-((tert-Butoxycarbonyl)amino)thiazol-4-yl)pent-2-enoic acid

Base Information

• Chemical Name: (Z)-2-(2-((tert-Butoxycarbonyl)amino)thiazol-4-yl)pent-2-enoic acid
• CAS No.: 86978-24-7
• Molecular Formula: C13H18N2O4S
• Molecular Weight: 298.363
• Hs Code.: 2942000000
• European Community (EC) Number: 430-100-3
• Nikkaji Number: J1.631.609A
• Mol file: 86978-24-7.mol

Synonyms:86978-24-7;(Z)-2-(2-((tert-Butoxycarbonyl)amino)thiazol-4-yl)pent-2-enoic acid;(Z)-2-(2-tert-Butoxycarbonylaminothiazol-4-yl)-2-pentenoic acid;(Z)-2-(2-t-butoxycarbonylaminothiazol-4-yl)-2-pentenoic acid;(Z)-2-[2-[(2-methylpropan-2-yl)oxycarbonylamino]-1,3-thiazol-4-yl]pent-2-enoic Acid;EC 430-100-3;(Z)-2-[[(1,1-Dimethylethoxy)carbonyl]amino]-alpha-propylidene-4-thiazoleacetic Acid;btpa;eatb;(Z)-2-(2-t-butoxycarbonylamino-4-thiazolyl)pent-2-enoic acid;(Z)-2-(2-tert-Butoxycarbonylamino-4-thiazolyl)-2-pentenoic acid;(Z)-2-(2-((tert-Butoxycarbonyl)amino)-thiazol-4-yl)pent-2-enoic acid;BAPA;SCHEMBL4755227;SCHEMBL4755230;AMY22347;BCP22683;(Z)-2-(2-((tert-Butoxycarbonyl)amino)thiazol-4-yl)pent-2-enoicacid;MFCD08458237;AKOS015896643;BCP9000634;DS-1869;CS-0153944;A841894;J-502579;(Z)-2-(2-(BOC-amino)thiazol-4-yl)pent-2-enoic acid;(Z)-2-(2-t-butoxycarbonylaminothiazol-4- yl) -2-pentenoic acid;(2Z)-2-(2-{[(tert-butoxy)carbonyl]amino}-1,3-thiazol-4-yl)pent-2-enoic acid;2-[2-(tert-butoxycarbonylamino)thiazol-4-yl]pent-2-enoic acid

Chemical Property of (Z)-2-(2-((tert-Butoxycarbonyl)amino)thiazol-4-yl)pent-2-enoic acid

Chemical Property:

• Appearance/Colour: white solid
• Melting Point: 159-161 °C
• Refractive Index: 1.583
• PKA: 3.34±0.36(Predicted)
• PSA: 116.76000
• Density: 1.279 g/cm³
• LogP: 3.44110
• Storage Temp.: Refrigerator
• Solubility.: Chloroform, Iso-propanol
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 6
• Exact Mass: 298.09872823
• Heavy Atom Count: 20
• Complexity: 404

Purity/Quality:

99% ^*data from raw suppliers

(Z)-2-[[(1,1-Dimethylethoxy)carbonyl]amino]-α-propylidene-4-thiazoleaceticAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC=C(C1=CSC(=N1)NC(=O)OC(C)(C)C)C(=O)O
• Isomeric SMILES: CC/C=C(/C1=CSC(=N1)NC(=O)OC(C)(C)C)\C(=O)O
• Uses: Intermediate for Cefcapene Cefcapene intermediate.

Technology Process of (Z)-2-(2-((tert-Butoxycarbonyl)amino)thiazol-4-yl)pent-2-enoic acid

There total 7 articles about (Z)-2-(2-((tert-Butoxycarbonyl)amino)thiazol-4-yl)pent-2-enoic acid 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: 90.0%

2-(2-tert-butoxycarbonylaminothiazol-4-yl)-2-pentenoic acid ethyl ester (158743-37-4) → (Z)-2-[2-(tert-butoxycarbonylamino)thiazol-4-yl]pent-2-enoic acid (86978-24-7)

Guidance literature:

2-(2-tert-butoxycarbonylaminothiazol-4-yl)-2-pentenoic acid ethyl ester; With sodium hydroxide; In water; isopropyl alcohol; at 65 ℃; for 1.5h;

With hydrogenchloride; In water; isopropyl alcohol; at 20 ℃; for 31h; pH=3 - 4;

DOI:10.1055/s-0033-1338954

Reference yield: 81.4%

ethyl (Z)-2-(2-aminothiazol-4-yl)pent-2-enoate + di-tert-butyl dicarbonate (24424-99-5) → (Z)-2-[2-(tert-butoxycarbonylamino)thiazol-4-yl]pent-2-enoic acid (86978-24-7)

Guidance literature:

ethyl (Z)-2-(2-aminothiazol-4-yl)pent-2-enoate; di-tert-butyl dicarbonate; With pyridine; In dichloromethane; at 30 - 35 ℃; for 8h;

With water; sodium hydroxide; In dichloromethane; at 65 - 70 ℃; for 4h;

With hydrogenchloride; In dichloromethane; water; at 30 - 35 ℃;

Reference yield: 80.2%

(Z)-2-(2-aminothiazol-4-yl)-2-pentenoic acid methyl ester + di-tert-butyl dicarbonate (24424-99-5) → (Z)-2-[2-(tert-butoxycarbonylamino)thiazol-4-yl]pent-2-enoic acid (86978-24-7)

Guidance literature:

(Z)-2-(2-aminothiazol-4-yl)-2-pentenoic acid methyl ester; di-tert-butyl dicarbonate; With pyridine; In dichloromethane; at 30 - 35 ℃; for 8h;

With water; sodium hydroxide; In dichloromethane; at 65 - 70 ℃; for 4h;

With hydrogenchloride; In water; at 30 - 35 ℃;

upstream raw materials:

2-(2-tert-butoxycarbonylaminothiazol-4-yl)-2-pentenoic acid ethyl ester

tert-butyl (2E)-2-[(tert-butoxycarbonyl)inimo]-4-(2-ethoxy-2-oxoethyl)-1,3-thiazole-3-(2H)-carboxylate

2-(2-tert-Butoxycarbonylamino-thiazol-4-yl)-3-tert-butoxycarbonyloxy-pentanoic acid ethyl ester

ethyl 2-(2-bromoacetyl)pent-2-enoate

Downstream raw materials:

diphenylmethyl 7β-<(Z)-2-(2-tert-butoxycarbonylaminothiazol-4-yl)-2-pentenoylamino>-3-acetoxymethyl-3-cephem-4-carboxylate

cefcapene pivoxil

((6R,7R)-3-((aminocarbonyl)oxy)methyl-7-((Z)-2-(2-tert-butoxycarbonylaminothiazol-4-yl)-2-pentenoyl)amino)-8-oxo-5-thio-1-azabicyclo[4.2.0]-oct-2-ene-2-carboxylic acid(2,2-dimethyloxypropoxymethyl)ester

cefcapene

Refernces

• 1、 -. "A head spore card side chain acid method for the preparation of". Paragraph 0016; 0017. . Retrieved 2016/11/14.
• 2、 Ishikura,Kubota,Minami,Hamashima,Nakashimizu,Motokawa,Yoshida. "Synthesis and structure-activity relationships of 7β-[(Z)-2-(2-aminothiazol-4-yl)-3-(substituted)-2- propenoyl-amino]-3-desacetoxymethylcephalosporins". . p. 453 - 465. Retrieved 2007/10/02.