3-(3-METHYL-4-NITROBENZYL)-L-HISTIDINE

Base Information

• Chemical Name: 3-(3-METHYL-4-NITROBENZYL)-L-HISTIDINE
• CAS No.: 114787-84-7
• Molecular Formula: C14H16 N4 O4 . 2 Cl H
• Molecular Weight: 377.22312
• Mol file: 114787-84-7.mol

Synonyms:3-(3-METHYL-4-NITROBENZYL)-L-HISTIDINE;3-(3-METHYL-4-NITROBENZYL)-HISTIDINE DIHYDROCHLORIDE, 98%

Chemical Property of 3-(3-METHYL-4-NITROBENZYL)-L-HISTIDINE

Chemical Property:

• Melting Point: 145-148 °C(lit.)
• PSA: 126.96000
• LogP: 3.12790

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 3-(3-METHYL-4-NITROBENZYL)-L-HISTIDINE

There total 4 articles about 3-(3-METHYL-4-NITROBENZYL)-L-HISTIDINE 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: 100.0%

N-<(1,1-dimethylethoxy)carbonyl>-3-<(3-methyl-4-nitrophenyl)methyl>-L-histidine methyl ester (114787-83-6) → 3-<(3-methyl-4-nitrophenyl)methyl>-L-histidine dihydrochloride (114787-84-7)

Guidance literature:

With hydrogenchloride; In methanol; for 1.5h; Heating;

DOI:10.1021/jm00115a014

Reference yield:

3-methyl-4-nitrobenzyl alcohol (80866-75-7) → 3-<(3-methyl-4-nitrophenyl)methyl>-L-histidine dihydrochloride (114787-84-7)

Guidance literature:

Multi-step reaction with 3 steps

1: (iPr)2NEt / CH₂Cl₂ / 0.5 h / -75 °C

2: 1.) CH₂Cl₂, from -75 deg C to RT, 8 h, 2.) CH₂Cl₂, pH 7, 1.5 h

3: 100 percent / 6 N HCl / methanol / 1.5 h / Heating

With hydrogenchloride; N-ethyl-N,N-diisopropylamine; In methanol; dichloromethane;

DOI:10.1021/jm00115a014

Reference yield:

Trifluoro-methanesulfonic acid 3-methyl-4-nitro-benzyl ester → 3-<(3-methyl-4-nitrophenyl)methyl>-L-histidine dihydrochloride (114787-84-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) CH₂Cl₂, from -75 deg C to RT, 8 h, 2.) CH₂Cl₂, pH 7, 1.5 h

2: 100 percent / 6 N HCl / methanol / 1.5 h / Heating

With hydrogenchloride; In methanol;

DOI:10.1021/jm00115a014

upstream raw materials:

N-<(1,1-dimethylethoxy)carbonyl>-3-<(3-methyl-4-nitrophenyl)methyl>-L-histidine methyl ester

3-methyl-4-nitrobenzyl alcohol

4-(2-tert-butoxycarbonylamino-2-methoxycarbonyl-ethyl)-1H-imidazole-1-carboxylic acid tert-butyl ester

Downstream raw materials:

(S)-5-diphenylacetyl-1-(3-methyl-4-nitrophenyl) methyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine-6-carboxylic acid

(S)-4,5,6,7-tetrahydro-1-<(3-methyl-4-nitrophenyl)methyl>-1H-imidazo<4,5-c>pyridine-6-carboxylic acid dihydrochloride

PD 123319 bistrifluoroacetate

5-(diphenylacetyl)-4,5,6,7-tetrahydro-1-<<3-methyl-4-<<(methylamino)carbonyl>amino>phenyl>methyl>-1H-imidazo<4,5-c>pyridine-6-carboxylic acid

Refernces

• 1、 Blankley, C. John,Hodges, John C.,Klutchko, Sylvester R.,Himmelsbach, Richard J.,Chucholowski, Alexander,et al.. "Synthesis and Structure-Activity Relationships of a Novel Series of Non-Peptide Angiotensin II Receptor Binding Inhibitors Specific for the AT2 Subtype". . p. 3248 - 3260. Retrieved 2007/10/02.