Fmoc-4-methyl-L-phenylalanine

Base Information

• Chemical Name: Fmoc-4-methyl-L-phenylalanine
• CAS No.: 199006-54-7
• Molecular Formula: C₂₅H₂₃NO₄
• Molecular Weight: 401.462
• Hs Code.: 29225090
• DSSTox Substance ID: DTXSID50427844
• Nikkaji Number: J3.574.505J
• Mol file: 199006-54-7.mol

Synonyms:199006-54-7;Fmoc-Phe(4-Me)-OH;Fmoc-4-methyl-L-phenylalanine;FMOC-L-4-Methylphe;Fmoc-L-4-Methylphenylalanine;Fmoc-4-Methy-L-Phenylalanine;(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-(4-methylphenyl)propanoic acid;MFCD00270197;N-FMOC-4-METHYL-L-PHENYLALANINE;Phenylalanine, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-4-methyl-;(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-(p-tolyl)propanoic acid;FMOC-D-4-METHYLPHENYLALANINE;nilwl09;Fmoc-4-Methyl-L-Phe-OH;N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-4-methyl-L-phenylalanine;SCHEMBL120602;DTXSID50427844;(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-(p-tolyl)propanoic acid;AKOS015837286;AKOS015912123;AC-9931;AM83432;CS-W016747;HY-W016031;DS-16172;F1032;J3.574.505J;A50202;EN300-1177814;A814052;J-012855;L-Phenylalanine, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-4-methyl-;N-ALPHA-(9-FLUORENYLMETHYLOXYCARBONYL)-4-METHYL-L-PHENYLALANINE;(2S)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-3-(4-methylphenyl)propanoic acid;(S)-2-(((9H-FLUOREN-9-YL)METHOXY)CARBONYLAMINO)-3-P-TOLYLPROPANOIC ACID

Chemical Property of Fmoc-4-methyl-L-phenylalanine

Chemical Property:

• Vapor Pressure: 1.08E-16mmHg at 25°C
• Melting Point: 168°C
• Refractive Index: 1.626
• Boiling Point: 629.1 °C at 760 mmHg
• PKA: 3.81±0.10(Predicted)
• Flash Point: 334.3 °C
• PSA: 75.63000
• Density: 1.255g/cm³
• LogP: 4.92030
• Storage Temp.: 2-8°C
• Solubility.: Soluble in Dimethylformamide(DMF).
• XLogP3: 5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 401.16270821
• Heavy Atom Count: 30
• Complexity: 578

Purity/Quality:

98%,99%, ^*data from raw suppliers

Fmoc-l-4-methylphe ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)CC(C(=O)O)NC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24
• Isomeric SMILES: CC1=CC=C(C=C1)C[C@@H](C(=O)O)NC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24
• Uses: N-Fmoc-4-methyl-L-phenylalanine is used as pharmaceutical intermediate.

Technology Process of Fmoc-4-methyl-L-phenylalanine

There total 3 articles about Fmoc-4-methyl-L-phenylalanine 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) + 4-methyl-L-phenylalanine (1991-87-3,4599-47-7,7758-37-4,49759-61-7) → (2S)-2-(9H-fluorene-9-ylmethoxycarbonylamino)-3-(4-methylphenyl)propanoic acid (204260-38-8,199006-54-7)

Guidance literature:

With sodium carbonate; In water; at 0 - 20 ℃; for 3h;

DOI:10.1002/anie.201610580

Reference yield:

(S)-2-(1,3-dioxoisoindolin-2-yl)-3-(p-tolyl)propanoic acid → (2S)-2-(9H-fluorene-9-ylmethoxycarbonylamino)-3-(4-methylphenyl)propanoic acid (204260-38-8,199006-54-7)

Guidance literature:

Multi-step reaction with 2 steps

1: hydrazine hydrate / methanol / 24 h / 20 °C

2: sodium carbonate / water / 3 h / 0 - 20 °C

With sodium carbonate; hydrazine hydrate; In methanol; water;

DOI:10.1002/anie.201610580

Reference yield:

4-tolyl iodide (624-31-7) → (2S)-2-(9H-fluorene-9-ylmethoxycarbonylamino)-3-(4-methylphenyl)propanoic acid (204260-38-8,199006-54-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 2-isobutoxy-4-methyl-6,7-dihydro-5H-cyclopenta[b]pyridine; palladium diacetate; silver(I) acetate; disodium phosphate heptahydrate; 1‐(6‐methoxypyridin‐3‐yl)ethan‐1‐one / 24 h / 100 °C / Sealed tube

2: hydrazine hydrate / methanol / 24 h / 20 °C

3: sodium carbonate / water / 3 h / 0 - 20 °C

With disodium phosphate heptahydrate; 2-isobutoxy-4-methyl-6,7-dihydro-5H-cyclopenta[b]pyridine; silver(I) acetate; palladium diacetate; sodium carbonate; hydrazine hydrate; 1‐(6‐methoxypyridin‐3‐yl)ethan‐1‐one; In methanol; water;

DOI:10.1002/anie.201610580

upstream raw materials:

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

4-methyl-L-phenylalanine

4-tolyl iodide

Downstream raw materials:

O-W-F-F(4-Me)-F-H(1-Bzl)-NH₂

O-W-F(4-Me)-I-F-H(1-Bzl)-NH₂

O-W-F-I-F(4-Me)-H(1-Bzl)-NH₂

C₃₄H₅₂N₆O₅

Refernces