1-(9H-fluoren-9-ylmethoxycarbonyl)-4-fluoropyrrolidine-2-carboxylic acid

Base Information

• Chemical Name: 1-(9H-fluoren-9-ylmethoxycarbonyl)-4-fluoropyrrolidine-2-carboxylic acid
• CAS No.: 203866-20-0
• Molecular Formula: C20H18FNO4
• Molecular Weight: 355.366
• Hs Code.: 29339900
• DSSTox Substance ID: DTXSID80405731
• Mol file: 203866-20-0.mol

Synonyms:Fmoc-trans-4-Fluoro-L-proline;1-(((9H-Fluoren-9-yl)methoxy)carbonyl)-4-fluoropyrrolidine-2-carboxylic acid;1520875-05-1;(4S)-1-Fmoc-4-fluoro-L-proline;MFCD03424224;MFCD08273756;starbld0009918;SCHEMBL1336767;DTXSID80405731;1-(9H-fluoren-9-ylmethoxycarbonyl)-4-fluoropyrrolidine-2-carboxylic acid;AB87896;SY065359;SY312534;FT-0679867;FT-0679869;(2R,4S)-1-Fmoc-4-fluoropyrrolidine-2-carboxylic Acid;1-[(9H-fluoren-9-ylmethoxy)carbonyl]-4-fluoropyrrolidine-2-carboxylic acid

Chemical Property of 1-(9H-fluoren-9-ylmethoxycarbonyl)-4-fluoropyrrolidine-2-carboxylic acid

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.646
• Boiling Point: 556.024 °C at 760 mmHg
• PKA: 3.48±0.40(Predicted)
• Flash Point: 290.073 °C
• PSA: 66.84000
• Density: 1.403 g/cm³
• LogP: 3.37040
• Storage Temp.: Store at?0-5°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:

98%, ^*data from raw suppliers

(2S,4R)-4-Fluoropyrrolidine-2-carboxylic acid, N-Fmoc protected ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(CN(C1C(=O)O)C(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24)F

Technology Process of 1-(9H-fluoren-9-ylmethoxycarbonyl)-4-fluoropyrrolidine-2-carboxylic acid

There total 17 articles about 1-(9H-fluoren-9-ylmethoxycarbonyl)-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: 95.5%

4-fluoro-pyrrolidine-1,2-dicarboxylic acid 1-(9H-fluoren-9-ylmethyl) ester 2-(2-oxo-2-phenyl-ethyl) ester (497073-98-0) → (2S,4R)-N-Fmoc-4-fluoroproline (203866-20-0,913820-87-8)

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,4R)-N-Fmoc-4-fluoroproline (203866-20-0,913820-87-8)

Guidance literature:

Multi-step reaction with 6 steps

1: 76 percent / Et₃N / CHCl₃ / 0 °C

2: 1.) PPh₃, DEAD, PhCO₂H; 2.) KOH / 1.) toluene; 2.) MeOH

3: 63 percent / DAST / CH₂Cl₂ / -78 deg C to r.t.

4: 99 percent / LiOH / acetonitrile; H₂O / Ambient temperature

5: TFA / CH₂Cl₂

6: Et₃N / methanol

With potassium hydroxide; lithium hydroxide; triethylamine; triphenylphosphine; 4,4'-diaminostilbene-2,2'-disulfonic acid; benzoic acid; trifluoroacetic acid; diethylazodicarboxylate; In methanol; dichloromethane; chloroform; water; acetonitrile;

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

Reference yield:

(fluorenylmethoxy)carbonyl chloride (28920-43-6) + (2S,4R)-4-fluoropyrrolidine-2-carboxylic acid (2438-57-5,2507-61-1,7553-49-3,21156-44-5,21156-75-2,60828-35-5,131176-02-8,913820-71-0) → (2S,4R)-N-Fmoc-4-fluoroproline (203866-20-0,913820-87-8)

Guidance literature:

With sodium hydrogencarbonate; In 1,4-dioxane; water; at 0 - 20 ℃; for 9h;

DOI:10.1002/anie.200805427

upstream raw materials:

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

(2S,4R)-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

Downstream raw materials:

C₃₉H₆₅FN₁₂O₈

Refernces

• 1、 Doi, Masamitsu,Nishi, Yoshinori,Kiritoshi, Naruto,Iwata, Tomoya,Nago, Mika,Nakano, Hiroaki,Uchiyama, Susumu,Nakazawa, Takashi,Wakamiya, Tateaki,Kobayashi, Yuji. "Simple and efficient syntheses of Boc- and Fmoc-protected 4(R)- and 4(S)-fluoroproline solely from 4(R)-hydroxyproline". . p. 8453 - 8459. Retrieved 2007/10/03.