(2S,4S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)-4-phenylpyrrolidine-2-carboxylic acid

Base Information

• Chemical Name: (2S,4S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)-4-phenylpyrrolidine-2-carboxylic acid
• CAS No.: 269078-71-9
• Molecular Formula: C₂₆H₂₃NO₄
• Molecular Weight: 413.473
• Hs Code.: 2924297099
• DSSTox Substance ID: DTXSID601152131
• Mol file: 269078-71-9.mol

Synonyms:269078-71-9;(2s,4s)-fmoc-4-phenyl-pyrrolidine-2-carboxylic acid;(2S,4S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)-4-phenylpyrrolidine-2-carboxylic acid;Fmoc-(2S,4S)-4-phenyl-pyrrolidine-2-carboxylic acid;(2S,4S)-1-(9H-fluoren-9-ylmethoxycarbonyl)-4-phenylpyrrolidine-2-carboxylic acid;(2S,4S)-1-{[(9H-fluoren-9-yl)methoxy]carbonyl}-4-phenylpyrrolidine-2-carboxylic acid;Fmoc-(2S,4S)-4-phenylpyrrolidine-2-carboxylic acid;SCHEMBL3576113;DTXSID601152131;MFCD01074697;AKOS015837341;AKOS015893217;AS-68828;CS-0060483;H11483;EN300-7379394;(2S,4S)-Fmoc-4-phenyl-pyrrolidine-2-carboxylic acid, AldrichCPR;1-(9H-Fluoren-9-ylmethyl) (2S,4S)-4-phenyl-1,2-pyrrolidinedicarboxylate;(2S,4S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)-4-phenylpyrrolidine-2-carboxylicacid

Chemical Property of (2S,4S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)-4-phenylpyrrolidine-2-carboxylic acid

Chemical Property:

• Boiling Point: 626.3±55.0 °C(Predicted)
• PKA: 3.85±0.40(Predicted)
• PSA: 66.84000
• Density: 1.299±0.06 g/cm3(Predicted)
• LogP: 4.81610
• Storage Temp.: Store at -15°C
• XLogP3: 4.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 413.16270821
• Heavy Atom Count: 31
• Complexity: 638

Purity/Quality:

97% ^*data from raw suppliers

(2S,4S)-Fmoc-4-phenyl-pyrrolidine-2-carboxylicacid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(CN(C1C(=O)O)C(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24)C5=CC=CC=C5
• Isomeric SMILES: C1[C@H](CN([C@@H]1C(=O)O)C(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24)C5=CC=CC=C5

Technology Process of (2S,4S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)-4-phenylpyrrolidine-2-carboxylic acid

There total 1 articles about (2S,4S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)-4-phenylpyrrolidine-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:

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) + cis-4-phenyl-L-proline (103290-40-0) → (2S,4R)-1-(tert-butoxycarbonyl)-4-phenylpyrrolidine-2-carboxylic acid (1093651-96-7,269078-71-9)

Guidance literature:

With sodium carbonate; In tetrahydrofuran; at 20 ℃;

Reference yield:

C11H15N2O3PolS + (2S)-Fmoc-4-phenylpyrrolidine-2-carboxylic acid (316833-44-0,269078-71-9) + N-(9-fluorenylmethoxycarbonyl)-N-methyl-L-alanine (84000-07-7) + (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3,3-dimethylbutanoic acid (132684-60-7) → C32H44N5O6PolS

Guidance literature:

C₁₁H₁₅N₂O₃PolS; (2S)-Fmoc-4-phenylpyrrolidine-2-carboxylic acid; With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In chloroform; at -20 ℃; for 8h; 4-sulfamylbutyryl AM resin Automated synthesizer; Microwave irradiation;

With piperidine; In N,N-dimethyl-formamide; 4-sulfamylbutyryl AM resin Automated synthesizer; Microwave irradiation;

N-(9-fluorenylmethoxycarbonyl)-N-methyl-L-alanine; (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3,3-dimethylbutanoic acid; Further stages;

DOI:10.1016/j.bmc.2013.06.055

Reference yield:

N-(fluoren-9-ylmethoxycarbonyl)glycine (29022-11-5) + Fmoc-Leu-OH (35661-60-0) + Fmoc-L-Pro(trans-4-Ph) (269078-71-9) + N-Fmoc L-Phe (35661-40-6) + Fmoc-(tBu)Asp-OH (71989-14-5) + Fmoc-Thr(tBu)-OH (71989-35-0,138797-71-4) → C52H73N9O17

Guidance literature:

Fmoc-Leu-OH; With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; for 0.75h; Automated synthesizer;

With piperidine; In N,N-dimethyl-formamide; Automated synthesizer;

N-(fluoren-9-ylmethoxycarbonyl)glycine; Fmoc-Leu-OH; Fmoc-L-Pro(trans-4-Ph); N-Fmoc L-Phe; Fmoc-(tBu)Asp-OH; Fmoc-Thr(tBu)-OH; Fmoc-Glu(Pg)-OH; Further stages;

DOI:10.1016/j.bmc.2020.115738

upstream raw materials:

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

cis-4-phenyl-L-proline

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