(R)-3-[Benzyl-((S)-1-phenyl-ethyl)-amino]-3-(6-chloro-5-methoxymethoxy-pyridin-2-yl)-propionic acid tert-butyl ester

Base Information

• Chemical Name: (R)-3-[Benzyl-((S)-1-phenyl-ethyl)-amino]-3-(6-chloro-5-methoxymethoxy-pyridin-2-yl)-propionic acid tert-butyl ester
• CAS No.: 199168-12-2
• Molecular Formula: C₂₉H₃₅ClN₂O₄
• Molecular Weight: 511.061
• Mol file: 199168-12-2.mol

Synonyms:(R)-3-[Benzyl-((S)-1-phenyl-ethyl)-amino]-3-(6-chloro-5-methoxymethoxy-pyridin-2-yl)-propionic acid tert-butyl ester

Chemical Property of (R)-3-[Benzyl-((S)-1-phenyl-ethyl)-amino]-3-(6-chloro-5-methoxymethoxy-pyridin-2-yl)-propionic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-3-[Benzyl-((S)-1-phenyl-ethyl)-amino]-3-(6-chloro-5-methoxymethoxy-pyridin-2-yl)-propionic acid tert-butyl ester

There total 5 articles about (R)-3-[Benzyl-((S)-1-phenyl-ethyl)-amino]-3-(6-chloro-5-methoxymethoxy-pyridin-2-yl)-propionic acid 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: 83.0%

(S)-N-benzyl-1-phenylethylamine (17480-69-2) + (E)-tert-butyl 3-(2-chloro-3-methoxymethoxy-6-pyridyl)prop-2-enoate (199168-11-1) → (R)-3-[Benzyl-((S)-1-phenyl-ethyl)-amino]-3-(6-chloro-5-methoxymethoxy-pyridin-2-yl)-propionic acid tert-butyl ester (199168-12-2)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; at -80 ℃; for 1h;

DOI:10.1021/ja973231n

Reference yield:

2-chloro-3-hydroxypyridine (6636-78-8) → (R)-3-[Benzyl-((S)-1-phenyl-ethyl)-amino]-3-(6-chloro-5-methoxymethoxy-pyridin-2-yl)-propionic acid tert-butyl ester (199168-12-2)

Guidance literature:

Multi-step reaction with 4 steps

1: NaI, t-BuOCl / acetonitrile; H₂O

2: K₂CO₃ / acetone / 50 °C

3: 90 percent / Pd(OAc)2, Et₃N / dimethylformamide / 60 °C

4: 83 percent / BuLi / tetrahydrofuran / 1 h / -80 °C

With palladium diacetate; n-butyllithium; tert-butylhypochlorite; potassium carbonate; triethylamine; sodium iodide; In tetrahydrofuran; water; N,N-dimethyl-formamide; acetone; acetonitrile;

DOI:10.1021/ja973231n

Reference yield:

tert-Butyl acrylate (1663-39-4,25232-27-3) → (R)-3-[Benzyl-((S)-1-phenyl-ethyl)-amino]-3-(6-chloro-5-methoxymethoxy-pyridin-2-yl)-propionic acid tert-butyl ester (199168-12-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / Pd(OAc)2, Et₃N / dimethylformamide / 60 °C

2: 83 percent / BuLi / tetrahydrofuran / 1 h / -80 °C

With palladium diacetate; n-butyllithium; triethylamine; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1021/ja973231n

upstream raw materials:

(S)-N-benzyl-1-phenylethylamine

(E)-tert-butyl 3-(2-chloro-3-methoxymethoxy-6-pyridyl)prop-2-enoate

tert-Butyl acrylate

2-chloro-3-hydroxypyridine