DL-Azetidine-2-carboxylic acid

Base Information

• Chemical Name: DL-Azetidine-2-carboxylic acid
• CAS No.: 20063-89-2
• Molecular Formula: C4H7NO2
• Molecular Weight: 101.10400
• Hs Code.: 29329990
• Mol file: 20063-89-2.mol

Synonyms:Azetidine-2-carboxylic ac...;AZETIDINE-2-CARBOXYLIC ACID 2517-4-6;D,L-AZETIDINE-2-CARBOXYLIC ACID;

Chemical Property of DL-Azetidine-2-carboxylic acid

Chemical Property:

• Melting Point: 200-202oC
• PSA: 49.33000
• LogP: -0.23830
• Storage Temp.: Refrigerator
• Solubility.: Water

Purity/Quality:

99% ^*data from raw suppliers

D,L-Azetidine-2-Carboxylic Acid ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 22-41
• Safety Statements: 26-39

MSDS Files:

SDS file from LookChem

Useful:

• Uses: DL-Azetidine-2-carboxylic acid is a four-membered ring analog of L-Proline,it is a useful intermediate in the synthesis of polypeptides.

Technology Process of DL-Azetidine-2-carboxylic acid

There total 28 articles about DL-Azetidine-2-carboxylic 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: 100.0%

[4-((2-acetylamino-4-oxo-butyryloxy)-diphenyl-methyl)phenoxy]-poly(styrene-co-divinylbenzene), copolymer 99:1, trityl loading: 1.47 mmol/g → Azetidine-2-carboxylic acid (2517-04-6,20063-89-2)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 0.5h;

DOI:10.1002/adsc.200303053

Reference yield: 100.0%

tert-butyl (2S)-azetidine-2-carboxylate (129740-14-3,208034-97-3) → (2S)-azetidine-2-carboxylic acid (2133-34-8,20063-89-2)

Guidance literature:

With trifluoroacetic acid; In 1,2-dichloro-ethane; at 0 - 20 ℃; for 6h;

DOI:10.3987/COM-18-14002

Reference yield: 100.0%

benzyl [1(1S,2S)]-1-(1-phenyl-ethyl)-azetidine-2-carboxylate (247051-66-7) → (2S)-azetidine-2-carboxylic acid (2133-34-8,20063-89-2)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; for 96h;

DOI:10.1021/jo0515881

upstream raw materials:

(2S)-1-benzoylazetidine-2-carboxylic acid

benzyl [1(1S,2S)]-1-(1-phenyl-ethyl)-azetidine-2-carboxylate

(S)-1-((S)-1-Phenyl-ethyl)-azetidine-2-carboxylic acid; hydrochloride

methyl (2S,αR)-N-α-methylbenzylazetidine-2-carboxylate

Downstream raw materials:

N-benzyloxycarbonyl-(S)-(-)-2-azetidine-carboxylic acid

(S)-2-Azetidincarbonsaeure-ethylester-hydrochlorid

(2S:3'S:3''S)-N-[N-(3-amino-3-carboxypropyl)-3-amino-3-carboxypropyl]-azetidine-2-carboxylic acid

(S)-1-(t-butoxycarbonyl)azetidine-2-carboxylic acid

Refernces

• 1、 Yamada,Emori,Kinoshita,Okada. "The synthesis of (±) azetidine 2 carboxylic acid and 2 pyrrolidinone derivatives". . p. 649 - 652. Retrieved 1973.
• 2、 Takaishi, Tomohiro,Wakisaka, Kyosuke,Vavricka, Christopher J.,Kiyota, Hiromasa,Izumi, Minoru. "Multigram-scale and column chromatography-free synthesis of L-azetidine-2-carboxylic acid for the synthesis of nicotianamine and its derivatives". . p. 2126 - 2134. Retrieved 2019/04/04.
• 3、 Ma, Sang-ho,Yoon, Doo Ha,Ha, Hyun-Joon,Lee, Won Koo. "Preparation of enantiopure 2-acylazetidines and their reactions with chloroformates". . p. 269 - 271. Retrieved 2007/10/03.