Fmoc-L-prolyl chloride

Base Information

• Chemical Name: Fmoc-L-prolyl chloride
• CAS No.: 103321-52-4
• Molecular Formula: C20H18 Cl N O3
• Molecular Weight: 355.821
• DSSTox Substance ID: DTXSID001153224
• Nikkaji Number: J1.053.008C
• Mol file: 103321-52-4.mol

Synonyms:FMOC-L-PROLYL CHLORIDE;103321-52-4;9H-fluoren-9-ylmethyl (2S)-2-carbonochloridoylpyrrolidine-1-carboxylate;(S)-(9H-Fluoren-9-yl)methyl 2-(chlorocarbonyl)pyrrolidine-1-carboxylate;Fmoc-L-Pro-OHChloride;Fmoc-L-Proline chloride;SCHEMBL3669756;DTXSID001153224;9H-Fluoren-9-ylmethyl (2S)-2-(chlorocarbonyl)-1-pyrrolidinecarboxylate

Chemical Property of Fmoc-L-prolyl chloride

Chemical Property:

• Melting Point: 90-92 °C
• Boiling Point: 503.6±43.0 °C(Predicted)
• PKA: -3.78±0.40(Predicted)
• PSA: 46.61000
• Density: 1.328±0.06 g/cm3(Predicted)
• LogP: 4.10320
• Storage Temp.: Store at 0°C
• XLogP3: 4.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 355.0975211
• Heavy Atom Count: 25
• Complexity: 503

Purity/Quality:

98%Min ^*data from raw suppliers

FMOC-L-PROLYL CHLORIDE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(N(C1)C(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24)C(=O)Cl
• Isomeric SMILES: C1C[C@H](N(C1)C(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24)C(=O)Cl

Technology Process of Fmoc-L-prolyl chloride

There total 4 articles about Fmoc-L-prolyl chloride 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: 78.6%

Fmoc-Pro-OH (71989-31-6) → (S)-N-(fluoren-9-ylmethoxycarbonyl)prolyl chloride (103321-52-4)

Guidance literature:

With thionyl chloride; N,N-dimethyl-formamide; In dichloromethane; for 1h; Ambient temperature;

DOI:10.1021/jo00369a042

Reference yield:

1-(((9H-fluoren-9-yl)methoxy)carbonyl)pyrrolidine-2-carboxylic acid (144829-96-9) → (9H-fluoren-9-yl)methyl 2-(chlorocarbonyl)pyrrolidine-1-carboxylate (103321-52-4)

Guidance literature:

With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; at 20 ℃;

Reference yield:

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) → (S)-N-(fluoren-9-ylmethoxycarbonyl)prolyl chloride (103321-52-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium carbonate / tetrahydrofuran; water / 48 h

1.2: pH 2 - 3

2.1: thionyl chloride / dichloromethane / 0.5 h / 20 °C

With thionyl chloride; sodium carbonate; In tetrahydrofuran; dichloromethane; water;

DOI:10.1016/j.tetasy.2011.03.016

upstream raw materials:

Fmoc-Pro-OH

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

L-proline

1-(((9H-fluoren-9-yl)methoxy)carbonyl)pyrrolidine-2-carboxylic acid

Downstream raw materials:

(S)-2-[(E)-(3-Phenyl-acryloyl)]-pyrrolidine-1-carboxylic acid 9H-fluoren-9-ylmethyl ester

(2S)-2-(2-bromophenylcarbamoyl)pyrrolidine-2-carboxylic acid 9H-fluoren-9-ylmethyl ester

N-(N-fluorenylmethoxycarbonyl-2S-prolyl)-glycine benzyl ester

Fmoc-Pro-Gly-Val-Gly-Val-OBzl

Refernces

• 1、 Lawer, Aggie,Epton, Ryan G.,Stephens, Thomas C.,Palate, Kleopas Y.,Lodi, Mahendar,Marotte, Emilie,Lamb, Katie J.,Sangha, Jade K.,Lynam, Jason M.,Unsworth, William P.. "Evaluating the Viability of Successive Ring-Expansions Based on Amino Acid and Hydroxyacid Side-Chain Insertion". . p. 12674 - 12683. Retrieved 2020.
• 2、 Chaume, Grégory,Simon, Julien,Lensen, Nathalie,Pytkowicz, Julien,Brigaud, Thierry,Miclet, Emeric. "Homochiral versus Heterochiral Trifluoromethylated Pseudoproline Containing Dipeptides: A Powerful Tool to Switch the Prolyl-Amide Bond Conformation". . p. 13602 - 13608. Retrieved 2017.
• 3、 Qu, Chengke,Zhao, Wenshan,Zhang, Lei,Cui, Yuanchen. "Preparation of immobilized L-prolinamide via enzymatic polymerization of phenolic L-prolinamide and evaluation of its catalytic performance for direct asymmetric aldol reaction". . p. 209 - 213. Retrieved 2014.
• 4、 Guo, Guozhang,Wu, Yufeng,Zhao, Xiaowei,Wang, Jing,Zhang, Lei,Cui, Yuanchen. "Polymerization of L-proline functionalized styrene and its catalytic performance as a supported organocatalyst for direct enantioselective aldol reaction". . p. 740 - 746. Retrieved 2016.
• 5、 -. "DIMERS FOR USE IN SYNTHESIS OF PEPTIDOMIMETICS". Paragraph 00322-00324. . Retrieved 2021/11/13.