1-(9H-fluoren-9-ylmethoxycarbonyl)pyrrolidine-2-carboxylic acid

Base Information

• Chemical Name: 1-(9H-fluoren-9-ylmethoxycarbonyl)pyrrolidine-2-carboxylic acid
• CAS No.: 71989-31-6
• Molecular Formula: C20H19NO4
• Molecular Weight: 337.375
• Hs Code.: 2933 99 80
• European Community (EC) Number: 276-259-0
• NSC Number: 334294
• Nikkaji Number: J1.959.214F
• ChEMBL ID: CHEMBL1462646
• Mol file: 71989-31-6.mol

Synonyms:Fmoc-DL-Pro-OH;Fmoc-DL-proline;144829-96-9;(((9H-fluoren-9-yl)methoxy)carbonyl)proline;1-(((9H-fluoren-9-yl)methoxy)carbonyl)pyrrolidine-2-carboxylic acid;1-{[(9H-fluoren-9-yl)methoxy]carbonyl}pyrrolidine-2-carboxylic acid;Fmoc-L-Pro-OH;MFCD00037122;MFCD00077067;Fmoc-L-prolone;Fmoc Pro;NSC334294;1-(9H-fluoren-9-ylmethoxycarbonyl)pyrrolidine-2-carboxylic acid;Maybridge4_003416;Oprea1_362266;MLS000850745;SCHEMBL1002927;CHEMBL1462646;ZPGDWQNBZYOZTI-UHFFFAOYSA-N;HMS1530L06;HMS2790K15;EINECS 276-259-0;AKOS001309877;AKOS017278328;AB01584;AB02952;CCG-237322;NSC 334294;NSC-334294;SMR000456762;SY012632;SY013091;1-(9H-Fluorene-9-ylmethoxycarbonyl)proline;9-FLUORENYLMETHOXYCARBONYL-L-PROLINE;CS-0446839;FT-0629871;FT-0629931;EN300-20841;F78654;BRD-A42403850-001-01-2;Z104483550;1-(((9H-fluoren-9-yl)methoxy)carbonyl)pyrrolidine-2-carboxylicacid;1-[(9H-fluoren-9-ylmethoxy)carbonyl]pyrrolidine-2-carboxylic acid;1-(9H-Fluoren-9-ylmethyl) hydrogen (S)-pyrrolidine-1,2-dicarboxylate;InChI=1/C20H19NO4/c22-19(23)18-10-5-11-21(18)20(24)25-12-17-15-8-3-1-6-13(15)14-7-2-4-9-16(14)17/h1-4,6-9,17-18H,5,10-12H2,(H,22,23

Chemical Property of 1-(9H-fluoren-9-ylmethoxycarbonyl)pyrrolidine-2-carboxylic acid

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 7.19E-13mmHg at 25°C
• Melting Point: 117-118 °C(lit.)
• Refractive Index: -32.5 ° (C=1, DMF)
• Boiling Point: 548.6 °C at 760 mmHg
• PKA: 3.95±0.20(Predicted)
• Flash Point: 285.6 °C
• PSA: 66.84000
• Density: 1.328 g/cm³
• LogP: 3.42240
• Storage Temp.: 2-8°C
• Solubility.: Soluble in methanol. (almost transparency.)
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 337.13140809
• Heavy Atom Count: 25
• Complexity: 500

Purity/Quality:

99% ^*data from raw suppliers

Fmoc-L-proline 99+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(N(C1)C(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24)C(=O)O
• Uses: L-Proline-N-Fmoc is N-Fmoc protected L-Proline (P755995) which is an amino acid and precursor (with vitamin C) for collagen, the building block of the structure of tendons, ligaments, arteries, veins and muscles. It is important in wound healing.

Technology Process of 1-(9H-fluoren-9-ylmethoxycarbonyl)pyrrolidine-2-carboxylic acid

There total 22 articles about 1-(9H-fluoren-9-ylmethoxycarbonyl)pyrrolidine-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: 97.0%

Fmoc-Pro-OEt → Fmoc-Pro-OH (71989-31-6)

Guidance literature:

With magnesium iodide; In tetrahydrofuran; at 120 ℃; for 1h; chemoselective reaction; Inert atmosphere; Microwave irradiation; Sealed tube;

DOI:10.1002/chem.201501799

Reference yield: 95.0%

(fluorenylmethoxy)carbonyl chloride (28920-43-6) + L-proline (147-85-3,25191-13-3,37159-97-0,4305-67-3,4607-28-7) → Fmoc-Pro-OH (71989-31-6)

Guidance literature:

Reference yield: 95.0%

1-((9H-fluoren-9-yl)methyl) 2-benzyl (S)-pyrrolidine-1,2-dicarboxylate (1298116-72-9) → Fmoc-Pro-OH (71989-31-6)

Guidance literature:

With hydrogen; In ethanol; for 0.833333h;

DOI:10.1039/c0ob00962h

upstream raw materials:

(fluorenylmethoxy)carbonyl chloride

L-proline

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

(9-fluorenyl)methyl pentafluorophenyl carbonate

Downstream raw materials:

Fmoc-L-proline pentafluorophenyl ester

Fmoc-Pro-ODhbt

Z-L-Phe-L-Val-L-Pro-NH₂

Refernces

• 1、 Popovici-Muller, Janeta,Lemieux, René M.,Artin, Erin,Saunders, Jeffrey O.,Salituro, Francesco G.,Travins, Jeremy,Cianchetta, Giovanni,Cai, Zhenwei,Zhou, Ding,Cui, Dawei,Chen, Ping,Straley, Kimberly,Tobin, Erica,Wang, Fang,David, Muriel D.,Penard-Lacronique, Virginie,Quivoron, Cyril,Saada, Véronique,De Botton, Stéphane,Gross, Stefan,Dang, Lenny,Yang, Hua,Utley, Luke,Chen, Yue,Kim, Hyeryun,Jin, Shengfang,Gu, Zhiwei,Yao, Gui,Luo, Zhiyong,Lv, Xiaobing,Fang, Cheng,Yan, Liping,Olaharski, Andrew,Silverman, Lee,Biller, Scott,Su, Shin-San M.,Yen, Katharine. "Discovery of AG-120 (Ivosidenib): A First-in-Class Mutant IDH1 Inhibitor for the Treatment of IDH1 Mutant Cancers". supporting information. p. 300 - 305. Retrieved 2018/04/20.
• 2、 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 2016/08/01.