Fmoc-L-Aspartic acid 4-methyl ester

Base Information

• Chemical Name: Fmoc-L-Aspartic acid 4-methyl ester
• CAS No.: 145038-53-5
• Molecular Formula: C20H19NO6
• Molecular Weight: 369.374
• Mol file: 145038-53-5.mol

Synonyms:N-9-Fluorenylmethoxycarbonylasparticacid b-methyl ester;Fmoc-Asp(Ome)-OH;

Chemical Property of Fmoc-L-Aspartic acid 4-methyl ester

Chemical Property:

• Melting Point: 122-125 °C(Solv: hexane (110-54-3))
• Refractive Index: 1.596
• Boiling Point: 613.712 °C at 760 mmHg
• PKA: 3.54±0.23(Predicted)
• Flash Point: 324.962 °C
• PSA: 101.93000
• Density: 1.323 g/cm³
• LogP: 2.93230
• Storage Temp.: 2-8°C
• Solubility.: Chloroform, Methanol (Slightly)

Purity/Quality:

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

Fmoc-Asparticacid4-methylester >95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Fmoc-Asp(OMe)-OH is a useful research intermediate used in the solid phase synthesis of peptides as selective caspase-3 peptide inhibitors.

Technology Process of Fmoc-L-Aspartic acid 4-methyl ester

There total 5 articles about Fmoc-L-Aspartic acid 4-methyl ester 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: 92.0%

C23H23NO6 → (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-4-methoxy-4-oxobutanoic acid (145038-53-5)

Guidance literature:

With triethylsilane; palladium on activated charcoal; In methanol; for 0.0833333h;

DOI:10.1021/jo0706123

Reference yield: 82.0%

methanol (67-56-1) + L-Aspartic acid (56-84-8,25608-40-6,27881-03-4,32505-46-7,52526-39-3) + N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) → (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-4-methoxy-4-oxobutanoic acid (145038-53-5)

Guidance literature:

methanol; L-Aspartic acid; With acetyl chloride; at 20 ℃; for 18h; Cooling with ice;

With sodium carbonate; In water;

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide; In 1,4-dioxane; water; at 5 - 20 ℃;

Reference yield:

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) + (+)-β-methyl-L-aspartate hydrochloride (16856-13-6) + dimethyl L-aspartate hydrochloride (32213-95-9) → (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-4-methoxy-4-oxobutanoic acid (145038-53-5)

Guidance literature:

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide; (+)-β-methyl-L-aspartate hydrochloride; dimethyl L-aspartate hydrochloride; With water; sodium carbonate; In 1,4-dioxane; at 5 - 20 ℃; Cooling with ice;

With hydrogenchloride; In 1,4-dioxane; water;

upstream raw materials:

(S)-3-(((9H-fluoren-9-yl)methoxy)carbonylamino)-4-(allyloxy)-4-oxobutanoic acid

methanol

L-Aspartic acid

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

Downstream raw materials:

L-Aspartic acid

methyl N¹-[2-[(4-chlorophenyl)carbonyl]-4-(methyloxy)phenyl]-N²-{[(9H-fluoren-9-ylmethyl)oxy]carbonyl}-L-α-asparaginate

methyl 2-[(3S,2Z)-2-(acetylhydrazono)-5-(4-chlorophenyl)-7-(methyloxy)-1,3-dihydro-1,4-benzodiazepin-3-yl]acetate

Refernces

• 1、 -. "PROCESSES FOR PREPARING AMINO-SUBSTITUTED GAMMA-LACTAMS". Page/Page column 35; 36; 37. . Retrieved 2010/10/03.
• 2、 Mandal, Pijus K.,McMurray, John S.. "Pd-C-induced catalytic transfer hydrogenation with triethylsilane". . p. 6599 - 6601. Retrieved 2008/02/10.