(2S)-N-{(1R)-2-azido-1-[4-(2-methylpentyloxy)phenyl]ethyl}-2-phenylpropanamide

Base Information

• Chemical Name: (2S)-N-{(1R)-2-azido-1-[4-(2-methylpentyloxy)phenyl]ethyl}-2-phenylpropanamide
• CAS No.: 1287286-06-9
• Molecular Formula: C₂₃H₃₀N₄O₂
• Molecular Weight: 394.517
• Mol file: 1287286-06-9.mol

Synonyms:(2S)-N-{(1R)-2-azido-1-[4-(2-methylpentyloxy)phenyl]ethyl}-2-phenylpropanamide

Chemical Property of (2S)-N-{(1R)-2-azido-1-[4-(2-methylpentyloxy)phenyl]ethyl}-2-phenylpropanamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S)-N-{(1R)-2-azido-1-[4-(2-methylpentyloxy)phenyl]ethyl}-2-phenylpropanamide

There total 8 articles about (2S)-N-{(1R)-2-azido-1-[4-(2-methylpentyloxy)phenyl]ethyl}-2-phenylpropanamide 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%

(S)-2-Phenylpropionic acid (7782-24-3) + (1R)-2-azido-1-[4-(2-methylpentyloxy)phenyl]ethanamine (1287286-02-5) → (2S)-N-{(1R)-2-azido-1-[4-(2-methylpentyloxy)phenyl]ethyl}-2-phenylpropanamide (1287286-06-9)

Guidance literature:

(S)-2-Phenylpropionic acid; (1R)-2-azido-1-[4-(2-methylpentyloxy)phenyl]ethanamine; With N-ethyl-N,N-diisopropylamine; HATU; In dichloromethane; at 0 - 20 ℃; for 3h; Inert atmosphere;

With sodium hydrogencarbonate; In dichloromethane; water;

Reference yield:

tert-butyl (1R)-2-hydroxy-1-[4-(2-methylpentyloxy)phenyl]ethylcarbamate (1286280-72-5) → (2S)-N-{(1R)-2-azido-1-[4-(2-methylpentyloxy)phenyl]ethyl}-2-phenylpropanamide (1287286-06-9)

Guidance literature:

Multi-step reaction with 4 steps

1: carbon tetrabromide; triphenylphosphine / tetrahydrofuran / 2 h / 20 °C

2: sodium azide / N,N-dimethyl-formamide / 1 h / 20 °C

3: trifluoroacetic acid / dichloromethane / 1 h / 20 °C

4: N-ethyl-N,N-diisopropylamine; HATU / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere

With sodium azide; carbon tetrabromide; N-ethyl-N,N-diisopropylamine; triphenylphosphine; HATU; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

Reference yield:

tert-butyl N-[(1R)-2-bromo-1-{4-[(2-methylpentyl)oxy]phenyl}-ethyl]carbamate (1287286-00-3) → (2S)-N-{(1R)-2-azido-1-[4-(2-methylpentyloxy)phenyl]ethyl}-2-phenylpropanamide (1287286-06-9)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium azide / N,N-dimethyl-formamide / 1 h / 20 °C

2: trifluoroacetic acid / dichloromethane / 1 h / 20 °C

3: N-ethyl-N,N-diisopropylamine; HATU / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere

With sodium azide; N-ethyl-N,N-diisopropylamine; HATU; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide;

upstream raw materials:

(S)-2-Phenylpropionic acid

(1R)-2-azido-1-[4-(2-methylpentyloxy)phenyl]ethanamine

methyl (R)-2-amino-2-(4-hydroxyphenyl)acetate hydrochloride

tert-butyl (1R)-2-hydroxy-1-[4-(2-methylpentyloxy)phenyl]ethylcarbamate

Downstream raw materials:

(2S)-N-((1R)-2-(dimethylamino)-1-(4-(2-methylpentyloxy)phenyl)ethyl)-2-phenylpropanamide trifluoroacetate

(2S)-N-((1R)-2-(cyclopropylmethylamino)-1-(4-(2-methylpentyloxy)phenyl)ethyl)-2-phenylpropanamide

(2S)-N-((1R)-2-((1-aminocyclopentyl)methylamino)-1-(4-(2-methylpentyloxy)phenyl)ethyl)-2-phenylpropanamide

t-butyl 1-(((2R)-2-(4-(2-methylpentyloxy)phenyl)-2-((S)-2-phenylpropanamido)ethylamino)methyl)-cyclopentylcarbamate