(3S,4S)-3-amino-4-(hydroxymethyl)azetidin-2-one acetic acid

Base Information

• Chemical Name: (3S,4S)-3-amino-4-(hydroxymethyl)azetidin-2-one acetic acid
• CAS No.: 1380109-66-9
• Molecular Formula: C₂H₄O₂*C₄H₈N₂O₂
• Molecular Weight: 176.172
• Mol file: 1380109-66-9.mol

Synonyms:

Chemical Property of (3S,4S)-3-amino-4-(hydroxymethyl)azetidin-2-one acetic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4S)-3-amino-4-(hydroxymethyl)azetidin-2-one acetic acid

There total 1 articles about (3S,4S)-3-amino-4-(hydroxymethyl)azetidin-2-one acetic 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:

(3S,4S)-3-benzyloxycarbonylamino-4-hydroxymethyl-2-azetidinone (99397-29-2) + acetic acid (64-19-7,77671-22-8) → (3S,4S)-3-amino-4-(hydroxymethyl)azetidin-2-one acetic acid (1380109-66-9)

Guidance literature:

With hydrogen; palladium(II) hydroxide; In ethanol; at 25 ℃; for 16h; under 2585.81 Torr; Inert atmosphere;

Reference yield:

(3S,4S)-3-amino-4-(hydroxymethyl)azetidin-2-one acetic acid (1380109-66-9) → C42H49N7O11S (1380110-56-4)

Guidance literature:

Multi-step reaction with 5 steps

1.1: triethylamine / acetonitrile / 0.08 h

2.1: triphenylphosphine; 1H-imidazole; iodine / dichloromethane / 15 h / 20 °C

3.1: triethylamine; tetrabutylammoniun azide / tetrahydrofuran; 2-methyltetrahydrofuran / 17 h / 20 - 35 °C

4.1: palladium 10% on activated carbon / ethanol / 4 h / 20 °C / 1551.49 Torr

5.1: 1-hydroxy-pyrrolidine-2,5-dione; pyridine / dimethyl sulfoxide / 2 h / 20 °C

5.2: 2 h / 20 °C / Inert atmosphere

With pyridine; 1H-imidazole; 1-hydroxy-pyrrolidine-2,5-dione; palladium 10% on activated carbon; iodine; tetrabutylammoniun azide; triethylamine; triphenylphosphine; In tetrahydrofuran; 2-methyltetrahydrofuran; ethanol; dichloromethane; dimethyl sulfoxide; acetonitrile;

DOI:10.1021/jm400560z

Reference yield:

(3S,4S)-3-amino-4-(hydroxymethyl)azetidin-2-one acetic acid (1380109-66-9) → C47H60N8O14S2 (1380111-41-0)

Guidance literature:

Multi-step reaction with 6 steps

1: triethylamine / acetonitrile / 0.08 h

2: triphenylphosphine; 1H-imidazole; iodine / dichloromethane / 15 h / 20 °C

3: triethylamine; tetrabutylammoniun azide / tetrahydrofuran; 2-methyltetrahydrofuran / 17 h / 20 - 35 °C

4: palladium 10% on activated carbon / ethanol / 4 h / 20 °C / 1551.49 Torr

5: triethylamine / tert-butyl alcohol; 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran

6: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 3 h / 0 - 5 °C

With 1H-imidazole; di-isopropyl azodicarboxylate; palladium 10% on activated carbon; iodine; tetrabutylammoniun azide; triethylamine; triphenylphosphine; In tetrahydrofuran; 2-methyltetrahydrofuran; ethanol; dichloromethane; 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran; acetonitrile; tert-butyl alcohol;

DOI:10.1021/jm400560z

upstream raw materials:

(3S,4S)-3-benzyloxycarbonylamino-4-hydroxymethyl-2-azetidinone

acetic acid

Downstream raw materials:

C₄₃H₄₉N₉O₁₃S₂

2-((((Z)-2-(((2R,3S)-2-((3-((1,5-bis-(benzyloxy)-4-oxo-1,4-dihydropyridin-2-yl)methyl)ureido)-methyl)-4-oxoazetidin-3-yl)amino)-1-(2-((tert-butoxycarbonyl)amino)thiazol-4-yl)-2-oxoethylidene)-amino)oxy)-2-methylpropanoic acid tert-butyl ester

(2R,3S)-2-((3-((1,5-bis(benzyloxy)-4-oxo-1,4-dihydropyridin-2-yl)methyl)ureido)methyl)-3-((Z)-2-(((1-(tert-butoxy)-2-methyl-1-oxopropan-2-yl)oxy)imino)-2-(2-((tert-butoxycarbonyl)amino)thiazol-4-yl)acetamido)-4-oxoazetidine-1-sulfonic acid

C₄₅H₅₅N₇O₁₄S

Refernces

• 1、 Brown, Matthew F.,Mitton-Fry, Mark J.,Arcari, Joel T.,Barham, Rose,Casavant, Jeffrey,Gerstenberger, Brian S.,Han, Seungil,Hardink, Joel R.,Harris, Thomas M.,Hoang, Thuy,Huband, Michael D.,Lall, Manjinder S.,Lemmon, M. Megan,Li, Chao,Lin, Jian,McCurdy, Sandra P.,McElroy, Eric,McPherson, Craig,Marr, Eric S.,Mueller, John P.,Mullins, Lisa,Nikitenko, Antonia A.,Noe, Mark C.,Penzien, Joseph,Plummer, Mark S.,Schuff, Brandon P.,Shanmugasundaram, Veerabahu,Starr, Jeremy T.,Sun, Jianmin,Tomaras, Andrew,Young, Jennifer A.,Zaniewski, Richard P.. "Pyridone-conjugated monobactam antibiotics with gram-negative activity". supporting information. p. 5541 - 5552. Retrieved 2013/07/26.