(2S)-6-formamido-2-[(4R)-2-(2-hydroxyphenyl)-Δ²-1,3-oxazoline-4-carboxamido]hexanoic acid

Base Information

• Chemical Name: (2S)-6-formamido-2-[(4R)-2-(2-hydroxyphenyl)-Δ²-1,3-oxazoline-4-carboxamido]hexanoic acid
• CAS No.: 1378417-02-7
• Molecular Formula: C₁₇H₂₁N₃O₆
• Molecular Weight: 363.37
• Mol file: 1378417-02-7.mol

Synonyms:(2S)-6-formamido-2-[(4R)-2-(2-hydroxyphenyl)-Δ²-1,3-oxazoline-4-carboxamido]hexanoic acid

Chemical Property of (2S)-6-formamido-2-[(4R)-2-(2-hydroxyphenyl)-Δ²-1,3-oxazoline-4-carboxamido]hexanoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S)-6-formamido-2-[(4R)-2-(2-hydroxyphenyl)-Δ²-1,3-oxazoline-4-carboxamido]hexanoic acid

There total 11 articles about (2S)-6-formamido-2-[(4R)-2-(2-hydroxyphenyl)-Δ²-1,3-oxazoline-4-carboxamido]hexanoic 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: 53.0%

(2S)-benzyl 6-formamido-2-[(4R)-2-(2-hydroxyphenyl)-Δ2-1,3-oxazoline-4-carboxamido]hexanoate (1378235-13-2) → (2S)-6-formamido-2-[(4R)-2-(2-hydroxyphenyl)-Δ2-1,3-oxazoline-4-carboxamido]hexanoic acid (1378417-02-7)

Guidance literature:

With 10% Pd/C; hydrogen; In methanol; at 25 ℃; for 2h; under 2280.15 Torr;

DOI:10.1021/np200972s

Reference yield:

Fmoc-Lys-OH (105047-45-8) → (2S)-6-formamido-2-[(4R)-2-(2-hydroxyphenyl)-Δ2-1,3-oxazoline-4-carboxamido]hexanoic acid (1378417-02-7)

Guidance literature:

Multi-step reaction with 5 steps

1.1: acetic anhydride / 2 h / 0 - 60 °C / Inert atmosphere

1.2: 3 h / 0 - 25 °C / Inert atmosphere

2.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 25 °C / Inert atmosphere

3.1: piperidine / N,N-dimethyl-formamide / 1 h / 25 °C / Inert atmosphere

4.1: N-(3-dimethylaminopropyl)-N-ethylcarbodiimide / Inert atmosphere

5.1: 10% Pd/C; hydrogen / methanol / 2 h / 25 °C / 2280.15 Torr

With piperidine; 10% Pd/C; hydrogen; acetic anhydride; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/np200972s

Reference yield:

(2S)-({[(9H-fluoren-9-yl)methyloxy]carbonyl}amino)-6-formamidohexanoic acid (201004-23-1) → (2S)-6-formamido-2-[(4R)-2-(2-hydroxyphenyl)-Δ2-1,3-oxazoline-4-carboxamido]hexanoic acid (1378417-02-7)

Guidance literature:

Multi-step reaction with 4 steps

1: N-ethyl-N,N-diisopropylamine / dichloromethane / 25 °C / Inert atmosphere

2: piperidine / N,N-dimethyl-formamide / 1 h / 25 °C / Inert atmosphere

3: N-(3-dimethylaminopropyl)-N-ethylcarbodiimide / Inert atmosphere

4: 10% Pd/C; hydrogen / methanol / 2 h / 25 °C / 2280.15 Torr

With piperidine; 10% Pd/C; hydrogen; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/np200972s

upstream raw materials:

(2S)-benzyl 2-amino-6-formamidohexanoate

(4R)-2-[2-hydroxyphenyl]-Δ²-1,3-oxazoline-4-carboxylic acid

(2S)-benzyl 6-formamido-2-[(4R)-2-(2-hydroxyphenyl)-Δ²-1,3-oxazoline-4-carboxamido]hexanoate

Fmoc-Lys-OH