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

Base Information

• Chemical Name: (2S,4S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)-4-fluoropyrrolidine-2-carboxylic acid
• CAS No.: 203866-19-7
• Molecular Formula: C20H18 F N O4
• Molecular Weight: 355.366
• Hs Code.: 2933990090
• European Community (EC) Number: 820-552-3
• DSSTox Substance ID: DTXSID10373292
• Nikkaji Number: J932.818A
• Wikidata: Q76146268
• Mol file: 203866-19-7.mol

Synonyms:203866-19-7;(2S,4S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)-4-fluoropyrrolidine-2-carboxylic acid;(2S,4S)-1-(9H-fluoren-9-ylmethoxycarbonyl)-4-fluoropyrrolidine-2-carboxylic acid;(2S,4S)-Fmoc-4-fluoro-pyrrolidine-2-carboxylic acid;1228307-81-0;(2s,4s)-fmoc-4-fluoropyrrolidine-2-carboxylic acid;C20H18FNO4;Fmoc-cis-4-Fluoro-L-proline;(4S)-1-Fmoc-4-fluoro-L-proline;(2S,4S)-1-{[(9H-fluoren-9-yl)methoxy]carbonyl}-4-fluoropyrrolidine-2-carboxylic acid;Fmoc-cis-4-Fluoroproline;Fmoc-cis-Pro(4-F)-OH;SCHEMBL1335554;fmoc-(2s,4s)-4-fluoroproline;DTXSID10373292;MFCD07781261;AKOS015837374;AKOS015907886;FD21774;AS-49201;CS-0046771;C73843;EN300-657481;A879654;Fmoc-(2S,4S)-4-fluoro-pyrrolidine-2-carboxylic acid;1-(9H-Fluoren-9-ylmethoxycarbonyl)-4alpha-fluoro-L-proline;(2S,4S)-Fmoc-4-fluoro-pyrrolidine-2-carboxylic acid, AldrichCPR;(4S)-1-{[(9H-Fluoren-9-yl)methoxy]carbonyl}-4-fluoro-L-proline;(2S,4S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)-4-fluoropyrrolidine-2-carboxylicacid;1,2-Pyrrolidinedicarboxylicacid,4-fluoro-,1-(9H-fluoren-9-ylmethyl)ester,(2S,4S)-

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

Chemical Property:

• PSA: 66.84000
• LogP: 3.37040
• Storage Temp.: 2-8°C
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 355.12198622
• Heavy Atom Count: 26
• Complexity: 534

Purity/Quality:

97% ^*data from raw suppliers

Fmoc-cis-4-Fluoro-L-proline ^*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)F
• Isomeric SMILES: C1[C@@H](CN([C@@H]1C(=O)O)C(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24)F
• Uses: Fmoc-cis-4-fluoro-Pro-OH is a useful intermediate in the preparation of peptides containing substituted proline residues.

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

There total 13 articles about (2S,4S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)-4-fluoropyrrolidine-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: 89.8%

4-fluoro-pyrrolidine-1,2-dicarboxylic acid 1-(9H-fluoren-9-ylmethyl) ester 2-(2-oxo-2-phenyl-ethyl) ester (497073-96-8) → (2S,4S)-1-(((9H-fluoren-9-yl)methoxy)carbonyl)-4-fluoropyrrolidine-2-carboxylic acid (203866-19-7,913820-87-8)

Guidance literature:

With acetic acid; zinc; at 20 ℃;

DOI:10.1016/S0040-4020(02)01020-7

Reference yield:

L-4-hydroxyproline methyl ester hydrochloride (40216-83-9) → (2S,4S)-1-(((9H-fluoren-9-yl)methoxy)carbonyl)-4-fluoropyrrolidine-2-carboxylic acid (203866-19-7,913820-87-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 95 percent / Et₃N / CH₂Cl₂ / Ambient temperature

2: 81 percent / DAST / CH₂Cl₂ / -78 deg C to r.t.

3: 92 percent / LiOH / acetonitrile; H₂O / Ambient temperature

4: TFA / CH₂Cl₂

5: Et₃N / methanol

With lithium hydroxide; triethylamine; 4,4'-diaminostilbene-2,2'-disulfonic acid; trifluoroacetic acid; In methanol; dichloromethane; water; acetonitrile;

DOI:10.1016/S0040-4039(97)10793-6

Reference yield:

1-tert-butyl 2-methyl (2S,4S)-4-fluoropyrrolidine-1,2-dicarboxylate (203866-16-4) → (2S,4S)-1-(((9H-fluoren-9-yl)methoxy)carbonyl)-4-fluoropyrrolidine-2-carboxylic acid (203866-19-7,913820-87-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 92 percent / LiOH / acetonitrile; H₂O / Ambient temperature

2: TFA / CH₂Cl₂

3: Et₃N / methanol

With lithium hydroxide; triethylamine; trifluoroacetic acid; In methanol; dichloromethane; water; acetonitrile;

DOI:10.1016/S0040-4039(97)10793-6

upstream raw materials:

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

(2S,4S)-4-fluoropyrrolidine-2-carboxylic acid

4-fluoro-pyrrolidine-1,2-dicarboxylic acid 1-(9H-fluoren-9-ylmethyl) ester 2-(2-oxo-2-phenyl-ethyl) ester

1-(2,2-dimethyl-propionyl)-4-hydroxy-pyrrolidine-2-carboxylic acid