4-Oxazolidinecarboxylicacid,2-oxo-,methylester,(4R)-(9CI)

Base Information

• Chemical Name: 4-Oxazolidinecarboxylicacid,2-oxo-,methylester,(4R)-(9CI)
• CAS No.: 144542-43-8
• Molecular Formula: C5H7 N O4
• Molecular Weight: 145.115
• Mol file: 144542-43-8.mol

Synonyms:4-Oxazolidinecarboxylicacid, 2-oxo-, methyl ester, (R)-

Chemical Property of 4-Oxazolidinecarboxylicacid,2-oxo-,methylester,(4R)-(9CI)

Chemical Property:

• Boiling Point: 357.8±31.0 °C(Predicted)
• PKA: 10.82±0.40(Predicted)
• PSA: 68.12000
• Density: 1.320
• LogP: -1.09220
• Storage Temp.: 2-8°C

Purity/Quality:

98.5% ^*data from raw suppliers

(R)-Methyl2-oxooxazolidine-4-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 4-Oxazolidinecarboxylicacid,2-oxo-,methylester,(4R)-(9CI)

There total 25 articles about 4-Oxazolidinecarboxylicacid,2-oxo-,methylester,(4R)-(9CI) 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: 100.0%

bis(trichloromethyl) carbonate (32315-10-9) + R-(-)-serine methyl ester hydrochloride (5874-57-7) → (R)-2-oxo-oxazolidine-4-carboxylic acid methyl ester (144542-43-8)

Guidance literature:

In tetrahydrofuran; for 4h; Heating;

DOI:10.1021/ol0355783

Reference yield: 99.0%

bis(trichloromethyl) carbonate (32315-10-9) + methyl (2S)-2-amino-3-hydroxypropanoate hydrochloride (5680-80-8) → (S)-4-methoxycarbonyl-oxazolidin-2-one (96751-61-0,144542-43-8,132682-22-5)

Guidance literature:

With triethylamine; In dichloromethane; for 2.5h;

DOI:10.1002/chem.200601136

Reference yield: 95.0%

methyl (2S)-2-amino-3-hydroxypropanoate hydrochloride (5680-80-8) → (S)-4-methoxycarbonyl-oxazolidin-2-one (96751-61-0,144542-43-8,132682-22-5)

Guidance literature:

With bis(trichloromethyl) carbonate; triethylamine;

DOI:10.1021/jo101010c

upstream raw materials:

methanol

L-serin

bis(trichloromethyl) carbonate

(S)-2-oxo-oxazolidine-4-carboxylic acid

Downstream raw materials:

(S)-4-(hydroxydiphenylmethyl)oxazolidin-2-one

methyl (4S)-3-[(4-methoxyphenyl)methyl]-2-oxo-1,3-oxazolidine-4-carboxylate

(4S)-4-(hydroxymethyl)-1,3-oxazolidin-2-one

methyl (4S)-3-but-3-enyl-2-oxooxazolidine-4-carboxylate

Refernces

• 1、 Chevliakov, Maxim V.,Montgomery, John. "A stereodivergent approach to (-)-α-kainic acid and (+)-α-allokainic acid utilizing the complementarity of alkyne and allene cyclizations". . p. 11139 - 11143. Retrieved 1999.
• 2、 Chevliakov, Maxim V.,Montgomery, John. "Nickel and palladium catalysis in the stereoselective synthesis of functionalized pyrrolidines: Enantioselective formal synthesis of (+)-α- allokainic acid". . p. 3144 - 3146. Retrieved 1998.
• 3、 Adebomi, Victor,Sriram, Mahesh,Streety, Xavier,Raj, Monika. "Metal-Free Selective Modification of Secondary Amides: Application in Late-Stage Diversification of Peptides". supporting information. p. 6189 - 6193. Retrieved 2021/08/01.
• 4、 Kinoshita, Akihiro,Higashino, Masato,Yoshida, Koji,Aratani, Yoshiyuki,Kakuuchi, Akito,Hanada, Keisuke,Takeda, Hiroyuki,Naganawa, Atsushi,Matsuya, Hidekazu,Ohmoto, Kazuyuki. "Synthesis and evaluation of a potent, well-balanced EP2/EP3 dual agonist". . p. 200 - 214. Retrieved 2017/12/06.