D-Proline, 1-acetyl-, methyl ester (9CI)

Base Information

• Chemical Name: D-Proline, 1-acetyl-, methyl ester (9CI)
• CAS No.: 114376-47-5
• Molecular Formula: C8H13 N O3
• Molecular Weight: 171.196
• Mol file: 114376-47-5.mol

Synonyms:MethylN-acetyl-D-prolinate

Chemical Property of D-Proline, 1-acetyl-, methyl ester (9CI)

Chemical Property:

• Boiling Point: 113 °C (3 mmHg)
• PSA: 46.61000
• LogP: 0.10820

Purity/Quality:

(R)-Methyl1-acetylpyrrolidine-2-carboxylate 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of D-Proline, 1-acetyl-, methyl ester (9CI)

There total 24 articles about D-Proline, 1-acetyl-, methyl ester (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: 99.0%

methyl (2S)-pyrrolidine carboxylate (2577-48-2) + tetraacetoxysilane (562-90-3) → N-acetyl-L-proline methyl ester (2311-25-3,18800-83-4,27460-51-1,114376-47-5)

Guidance literature:

In tetrahydrofuran; at 50 ℃; for 3h;

DOI:10.1002/ejoc.201901660

Reference yield: 96.0%

methanol (67-56-1) + (S)-acetylproline (68-95-1) → N-acetyl-L-proline methyl ester (2311-25-3,18800-83-4,27460-51-1,114376-47-5)

Guidance literature:

With sulfuryl dichloride; for 24h; Ambient temperature;

DOI:10.1016/0040-4039(94)02233-2

Reference yield: 91.0%

acetic anhydride (108-24-7) + methyl (2R)-pyrrolidine-2-carboxylate (43041-12-9) → D-N-acetylproline methyl ester (114376-47-5)

Guidance literature:

With tris(pentafluorophenyl)borate; In neat (no solvent); at 20 ℃; for 0.05h; Green chemistry;

DOI:10.1016/j.tetlet.2014.01.124

upstream raw materials:

N-Acetyl-L-5-thioxoproline methyl ester

methanol

(S)-acetylproline

methyl (2S)-pyrrolidine carboxylate

Downstream raw materials:

cis-1-acetyl-5-phenylsulfanyl-pyrrolidine-2-carboxylic acid methyl ester

(2S)–N-acetyl-5-oxoproline methyl ester

(S)-1-Acetyl-5-hydroxy-pyrrolidine-2-carboxylic acid methyl ester

(2R,6R)-(+)-2-Methyl-1,4-diazabicyclo<4.3.0>nonan-5-one

Refernces

• 1、 Morisset, Eléonore,Chardon, Aurélien,Rouden, Jacques,Blanchet, Jér?me. "Phenysilane and Silicon Tetraacetate: Versatile Promotors for Amide Synthesis". supporting information. p. 388 - 392. Retrieved 2020/01/24.
• 2、 Kubyshkin, Vladimir,Budisa, Nediljko. "Hydrolysis, polarity, and conformational impact of C-terminal partially fluorinated ethyl esters in peptide models". . p. 2452 - 2457. Retrieved 2017/12/06.