(S)-2-(((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)methyl)-4-methylpentanoic acid

Base Information

• Chemical Name: (S)-2-(((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)methyl)-4-methylpentanoic acid
• CAS No.: 193887-45-5
• Molecular Formula: C22H25NO4
• Molecular Weight: 367.43800
• Hs Code.: 2924299090
• DSSTox Substance ID: DTXSID10464932
• Nikkaji Number: J1.876.555A
• Wikidata: Q82290506
• Mol file: 193887-45-5.mol

Synonyms:193887-45-5;(S)-2-(((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)methyl)-4-methylpentanoic acid;Fmoc-(S)-2-(aminomethyl)-4-methylpentanoic acid;(2S)-2-[(9H-fluoren-9-ylmethoxycarbonylamino)methyl]-4-methylpentanoic acid;(S)-FMOC-BETA2-HOMOLEUCINE;(2S)-2-[({[(9H-Fluoren-9-yl)methoxy]carbonyl}amino)methyl]-4-methylpentanoic acid;MFCD07372888;(S)-2-[(Fmoc-amino)methyl]-4-methylpentanoic Acid;DTXSID10464932;AKOS015950061;AS-32292;CS-0038228;A880235;(S)-2-(((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)methyl)-4-methylpentanoicacid

Chemical Property of (S)-2-(((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)methyl)-4-methylpentanoic acid

Chemical Property:

• Melting Point: 138-140 °C
• Boiling Point: 572.1±33.0 °C(Predicted)
• PKA: 4.45±0.21(Predicted)
• PSA: 79.12000
• Density: 1.188±0.06 g/cm3(Predicted)
• LogP: 4.47640
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• XLogP3: 4.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 8
• Exact Mass: 367.17835828
• Heavy Atom Count: 27
• Complexity: 498

Purity/Quality:

97% ^*data from raw suppliers

(S)-Fmoc-beta2-homoleucine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)CC(CNC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13)C(=O)O
• Isomeric SMILES: CC(C)C[C@@H](CNC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13)C(=O)O

Technology Process of (S)-2-(((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)methyl)-4-methylpentanoic acid

There total 9 articles about (S)-2-(((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)methyl)-4-methylpentanoic 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: 80.0%

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) + (2S)-([amino]methyl)-4-methylpentanoic acid (203854-56-2) → (2S)-isobutyl-3-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid (193887-45-5)

Guidance literature:

With sodium hydrogencarbonate; In tetrahydrofuran; water; at 20 ℃; for 2h;

DOI:10.1021/jo026738b

Reference yield:

benzyl 4-methyl-2-methylenepentanoate (118053-31-9) → (2S)-isobutyl-3-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid (193887-45-5)

Guidance literature:

Multi-step reaction with 4 steps

1: triethylamine / dimethylformamide / 24 h / 20 °C

2: LiHMDS / tetrahydrofuran / 0.5 h / -78 °C

3: HCOONH₄ / 10percent Pd/C / methanol / 60 °C

4: 80 percent / NaHCO₃ / tetrahydrofuran; H₂O / 2 h / 20 °C

With ammonium formate; sodium hydrogencarbonate; triethylamine; lithium hexamethyldisilazane; 10percent Pd/C; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide; 1: Michael addition;

DOI:10.1021/jo026738b

Reference yield:

2-acetyl-4-methyl-pentanoic acid benzyl ester (501330-86-5) → (2S)-isobutyl-3-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid (193887-45-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 94 percent / LiHMDS / tetrahydrofuran / 6 h / 20 °C

2: triethylamine / dimethylformamide / 24 h / 20 °C

3: LiHMDS / tetrahydrofuran / 0.5 h / -78 °C

4: HCOONH₄ / 10percent Pd/C / methanol / 60 °C

5: 80 percent / NaHCO₃ / tetrahydrofuran; H₂O / 2 h / 20 °C

With ammonium formate; sodium hydrogencarbonate; triethylamine; lithium hexamethyldisilazane; 10percent Pd/C; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide; 2: Michael addition;

DOI:10.1021/jo026738b

upstream raw materials:

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

(2S)-([amino]methyl)-4-methylpentanoic acid

benzyl 4-methyl-2-methylenepentanoate

2-acetyl-4-methyl-pentanoic acid benzyl ester