Fmoc-N-methyl-L-glutamic acid 5-tert-butyl ester

Base Information

• Chemical Name: Fmoc-N-methyl-L-glutamic acid 5-tert-butyl ester
• CAS No.: 200616-40-6
• Molecular Formula: C₂₅H₂₉NO₆
• Molecular Weight: 439.508
• Hs Code.: 2924297099
• Mol file: 200616-40-6.mol

Synonyms:Fmoc-N-Me-Glu(OtBu)-OH;N-(9-Fluorenylmethyloxycarbonyl)-N-methyl-L-glutamic acid 5-tert-butyl ester;

Chemical Property of Fmoc-N-methyl-L-glutamic acid 5-tert-butyl ester

Chemical Property:

• Appearance/Colour: solid
• Vapor Pressure: 7.58E-16mmHg at 25°C
• Melting Point: 116-119°C
• Refractive Index: 1.57
• Boiling Point: 612.3 °C at 760 mmHg
• PKA: 3.72±0.10(Predicted)
• Flash Point: 324.1 °C
• PSA: 93.14000
• Density: 1.22 g/cm³
• LogP: 4.44240
• Storage Temp.: -15°C

Purity/Quality:

≥98%,≥99%, ^*data from raw suppliers

Fmoc-N-Me-Glu(OtBu)-OH 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): N
• Hazard Codes: N
• Statements: 50/53
• Safety Statements: 60-61

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Fmoc-protected N-methyl amino acid. N-methyl amino acids have shown enhanced biological stability in peptides compared to standard amino acids.

Technology Process of Fmoc-N-methyl-L-glutamic acid 5-tert-butyl ester

There total 3 articles about Fmoc-N-methyl-L-glutamic acid 5-tert-butyl 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: 28.0%

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) + (R)-2-(((benzyloxy)carbonyl)(methyl)amino)-5-(tert-butoxy)-5-oxopentanoic acid (140837-98-5) → (R)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-5-(tert-butoxy)-5-oxopentanoic acid (200616-40-6)

Guidance literature:

(R)-2-(((benzyloxy)carbonyl)(methyl)amino)-5-(tert-butoxy)-5-oxopentanoic acid; With palladium 10% on activated carbon; hydrogen; In methanol; at 20 ℃; for 18h;

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide; With triethylamine; In water; acetonitrile; at 0 - 20 ℃; for 18h;

Reference yield:

(R)-2-amino-5-(tert-butoxy)-5-oxopentanoic acid (45125-00-6) → (R)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-5-(tert-butoxy)-5-oxopentanoic acid (200616-40-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: tetrahydrofuran; water / 2.5 h / 0 °C

2.1: sodium hydride / tetrahydrofuran; mineral oil / 24 h / 0 - 20 °C / Inert atmosphere

3.1: palladium 10% on activated carbon; hydrogen / methanol / 18 h / 20 °C

3.2: 18 h / 0 - 20 °C

With palladium 10% on activated carbon; hydrogen; sodium hydride; In tetrahydrofuran; methanol; water; mineral oil;

Reference yield:

N-(benzyloxy)carbonyl-D-glutamic acid 5-tert-butyl ester (51644-83-8) → (R)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-5-(tert-butoxy)-5-oxopentanoic acid (200616-40-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hydride / tetrahydrofuran; mineral oil / 24 h / 0 - 20 °C / Inert atmosphere

2.1: palladium 10% on activated carbon; hydrogen / methanol / 18 h / 20 °C

2.2: 18 h / 0 - 20 °C

With palladium 10% on activated carbon; hydrogen; sodium hydride; In tetrahydrofuran; methanol; mineral oil;

upstream raw materials:

(R)-2-amino-5-(tert-butoxy)-5-oxopentanoic acid

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

(R)-2-(((benzyloxy)carbonyl)(methyl)amino)-5-(tert-butoxy)-5-oxopentanoic acid

N-(benzyloxy)carbonyl-D-glutamic acid 5-tert-butyl ester

Downstream raw materials:

2-[(9H-fluoren-9-ylmethoxycarbonyl)-methyl-amino]-pentanedioic acid

Refernces