(1S,2S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)cyclopentanecarboxylic acid

Base Information

• Chemical Name: (1S,2S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)cyclopentanecarboxylic acid
• CAS No.: 359586-64-4
• Molecular Formula: C21H21 N O4
• Molecular Weight: 351.4
• Hs Code.: 2924299090
• DSSTox Substance ID: DTXSID60373282
• Nikkaji Number: J1.592.852B
• Wikidata: Q72477825
• Mol file: 359586-64-4.mol

Synonyms:359586-64-4;(1S,2S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)cyclopentanecarboxylic acid;(1S,2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)cyclopentane-1-carboxylic acid;(1S,2S)-FMOC-2-AMINOCYCLOPENTANE CARBOXYLIC ACID;Fmoc-(1S,2S)-2-aminocyclopentane carboxylic acid;(1S,2S)-2-({[(9H-Fluoren-9-yl)methoxy]carbonyl}amino)cyclopentane-1-carboxylic acid;(1S,2S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)cyclopentane-1-carboxylic acid;(1S,2S)-Fmoc-acpc;SCHEMBL6347068;DTXSID60373282;KTLDVIJVCPIJCM-HKUYNNGSSA-N;(1S,2S)-fmoc-acpc, AldrichCPR;MFCD04112694;AKOS025312264;(1S,2S)-2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}cyclopentane-1-carboxylic acid;AS-67292;CS-0149814;C74848;EN300-7372566;Fmoc-(1S,2S)-2-Aminocyclopentanecarboxylic acid;A874492;(1S,2S)-2-(Fmoc-amino)cyclopentanecarboxylic acid;(1S)-2beta-(9H-Fluorene-9-ylmethoxycarbonylamino)cyclopentane-1alpha-carboxylic acid;(1S,2S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)cyclopentanecarboxylicacid;(1S,2S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)cyclopentanecarboxylic acid

Chemical Property of (1S,2S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)cyclopentanecarboxylic acid

Chemical Property:

• Melting Point: 167 - 170°C
• Boiling Point: 584.8±39.0 °C(Predicted)
• PKA: 4.50±0.40(Predicted)
• PSA: 75.63000
• Density: 1.32±0.1 g/cm3(Predicted)
• LogP: 4.16930
• Storage Temp.: Store at?0-5°C
• Solubility.: Chloroform (Slightly, Sonicated), DMSO (Slightly), Methanol (Slightly, Sonicated
• XLogP3: 4.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 351.14705815
• Heavy Atom Count: 26
• Complexity: 514

Purity/Quality:

98% ^*data from raw suppliers

(1S,2S)-Fmoc-acpc ^*data from reagent suppliers

Safty Information:

• Hazard Codes: N
• Statements: 50
• Safety Statements: 61

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(C(C1)NC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24)C(=O)O
• Isomeric SMILES: C1C[C@@H]([C@H](C1)NC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24)C(=O)O
• Uses: (1S,2S)-Fmoc-acpc is used in preparation of chimeric (α/β + α)-peptide ligands for BH3-recognition cleft of the cancer-associated protein Bcl-xL.

Technology Process of (1S,2S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)cyclopentanecarboxylic acid

There total 8 articles about (1S,2S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)cyclopentanecarboxylic 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: 70.0%

(1S,2S)-2-hydroxymethyl-cyclopentyl-(9H-fluoren-9-ylmethoxy)-carbamate (359586-63-3) → (1S,2S)-2-(9H-fluoren-9-ylmethoxycarbonyl)amino-cyclopentanecarboxylic acid (359586-64-4,282524-97-4,352707-76-7)

Guidance literature:

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; tetrabutylammomium bromide; In dichloromethane; water; for 1h;

DOI:10.1021/jo010279h

Reference yield:

2-ethoxycarbonyl-1-cyclopentanone (611-10-9) → (1S,2S)-2-(9H-fluoren-9-ylmethoxycarbonyl)amino-cyclopentanecarboxylic acid (359586-64-4,282524-97-4,352707-76-7)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 85 percent / TsOH / benzene / 16 h / Heating

2.1: Na / tetrahydrofuran; propan-2-ol

2.2: 20 percent / 4N HCl / diethyl ether; dioxane / 2 h / 0 °C

3.1: 0.6 percent / HCO₂NH₄ / Pd/C / methanol / Heating

4.1: 1.1 g / NaHCO₃ / acetone / 24 h

5.1: 70 percent / TEMPO; nBu₄NBr; NaOCl / CH₂Cl₂; H₂O / 1 h

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; tetrabutylammomium bromide; ammonium formate; sodium; sodium hydrogencarbonate; toluene-4-sulfonic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; isopropyl alcohol; acetone; benzene;

DOI:10.1021/jo010279h

Reference yield:

2-[(S)-1-phenylethylamino]-cyclopent-1-enecarboxylic acid ethyl ester (53898-02-5) → (1S,2S)-2-(9H-fluoren-9-ylmethoxycarbonyl)amino-cyclopentanecarboxylic acid (359586-64-4,282524-97-4,352707-76-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: Na / tetrahydrofuran; propan-2-ol

1.2: 20 percent / 4N HCl / diethyl ether; dioxane / 2 h / 0 °C

2.1: 0.6 percent / HCO₂NH₄ / Pd/C / methanol / Heating

3.1: 1.1 g / NaHCO₃ / acetone / 24 h

4.1: 70 percent / TEMPO; nBu₄NBr; NaOCl / CH₂Cl₂; H₂O / 1 h

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; tetrabutylammomium bromide; ammonium formate; sodium; sodium hydrogencarbonate; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; isopropyl alcohol; acetone;

DOI:10.1021/jo010279h

upstream raw materials:

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

(1S,2S)-2-aminocyclopentanecarboxylic acid hydrochloride

(1S,2S)-2-hydroxymethyl-cyclopentyl-(9H-fluoren-9-ylmethoxy)-carbamate

2-[(S)-1-phenylethylamino]-cyclopent-1-enecarboxylic acid ethyl ester

Downstream raw materials:

C₂₆H₄₆N₄O

Refernces