(S)-2-Amino-3-(2-benzyloxy-5-nitro-phenyl)-propionic acid

Base Information

• Chemical Name: (S)-2-Amino-3-(2-benzyloxy-5-nitro-phenyl)-propionic acid
• CAS No.: 1027149-76-3
• Molecular Formula: C₁₆H₁₆N₂O₅
• Molecular Weight: 316.313
• Mol file: 1027149-76-3.mol

Synonyms:

Chemical Property of (S)-2-Amino-3-(2-benzyloxy-5-nitro-phenyl)-propionic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-Amino-3-(2-benzyloxy-5-nitro-phenyl)-propionic acid

There total 6 articles about (S)-2-Amino-3-(2-benzyloxy-5-nitro-phenyl)-propionic 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:

(S)-2-(Benzhydrylidene-amino)-3-(2-benzyloxy-5-nitro-phenyl)-1-((1R,5S,7S)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-propan-1-one (1026486-04-3) → (S)-2-Amino-3-(2-benzyloxy-5-nitro-phenyl)-propionic acid (1027149-76-3)

Guidance literature:

With lithium hydroxide; tetrabutylammomium bromide; lithium bromide; In acetonitrile; for 3h; Ambient temperature;

DOI:10.1021/jo00108a023

Reference yield:

2-hydroxy-5-nitrobenzyl alcohol (39224-61-8) → (S)-2-Amino-3-(2-benzyloxy-5-nitro-phenyl)-propionic acid (1027149-76-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 90 percent / NaH / tetrahydrofuran; dimethylformamide / 1.) 30-40 deg C, 30 min, 2.) r.t., 2 h

2: Et₃N / tetrahydrofuran / 1 h / 0 °C

3: NaI / acetone / 2 h / Ambient temperature

4: 87 percent / 10percent aq. NaOH, tetrabutylammonium hydrogen sulfate / CH₂Cl₂

5: aq. LiOH, LiBr, tetrabutylammonium bromide / acetonitrile / 3 h / Ambient temperature

With lithium hydroxide; sodium hydroxide; tetrabutylammomium bromide; tetra(n-butyl)ammonium hydrogensulfate; sodium hydride; triethylamine; sodium iodide; lithium bromide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetone; acetonitrile;

DOI:10.1021/jo00108a023

Reference yield:

benzyl bromide (100-39-0) → (S)-2-Amino-3-(2-benzyloxy-5-nitro-phenyl)-propionic acid (1027149-76-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 90 percent / NaH / tetrahydrofuran; dimethylformamide / 1.) 30-40 deg C, 30 min, 2.) r.t., 2 h

2: Et₃N / tetrahydrofuran / 1 h / 0 °C

3: NaI / acetone / 2 h / Ambient temperature

4: 87 percent / 10percent aq. NaOH, tetrabutylammonium hydrogen sulfate / CH₂Cl₂

5: aq. LiOH, LiBr, tetrabutylammonium bromide / acetonitrile / 3 h / Ambient temperature

With lithium hydroxide; sodium hydroxide; tetrabutylammomium bromide; tetra(n-butyl)ammonium hydrogensulfate; sodium hydride; triethylamine; sodium iodide; lithium bromide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetone; acetonitrile;

DOI:10.1021/jo00108a023

upstream raw materials:

(S)-2-(Benzhydrylidene-amino)-3-(2-benzyloxy-5-nitro-phenyl)-1-((1R,5S,7S)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-propan-1-one

2-hydroxy-5-nitrobenzyl alcohol

benzyl bromide

(2-(benzyloxy)-5-nitrophenyl)methanol

Downstream raw materials:

(S)-2-[(S)-3-(2-Benzyloxy-5-nitro-phenyl)-2-tert-butoxycarbonylamino-propionylamino]-propionic acid methyl ester

Ac-L-o-Nip(Bn)-Ala-OMe

(S)-2-[(S)-2-Amino-3-(2-benzyloxy-5-nitro-phenyl)-propionylamino]-propionic acid methyl ester

L-o-Tyr hydrochloride