L-Histidine, 3-(phenylmethyl)-, dihydrochloride

Base Information

• Chemical Name: L-Histidine, 3-(phenylmethyl)-, dihydrochloride
• CAS No.: 109013-61-8
• Molecular Formula: C13H15 N3 O2 . 2 Cl H
• Molecular Weight: 318.2
• Hs Code.: 2933290090
• DSSTox Substance ID: DTXSID00550474
• Mol file: 109013-61-8.mol

Synonyms:L-Histidine, 3-(phenylmethyl)-, dihydrochloride;109013-61-8;(2S)-2-amino-3-(3-benzylimidazol-4-yl)propanoic acid;dihydrochloride;(S)-2-Amino-3-(1-benzyl-1H-imidazol-5-yl)propanoic acid dihydrochloride;DTXSID00550474;AKOS015962523;AC-17185;3-Benzyl-L-histidine--hydrogen chloride (1/2);J-002220

Chemical Property of L-Histidine, 3-(phenylmethyl)-, dihydrochloride

Chemical Property:

• PSA: 81.14000
• LogP: 3.19010
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 317.0697822
• Heavy Atom Count: 20
• Complexity: 279

Purity/Quality:

97% ^*data from raw suppliers

3-(PHENYLMETHYL)-L-HISTIDINE DIHYDROCHLORIDE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)CN2C=NC=C2CC(C(=O)O)N.Cl.Cl
• Isomeric SMILES: C1=CC=C(C=C1)CN2C=NC=C2C[C@@H](C(=O)O)N.Cl.Cl

Technology Process of L-Histidine, 3-(phenylmethyl)-, dihydrochloride

There total 11 articles about L-Histidine, 3-(phenylmethyl)-, dihydrochloride 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: 95.0%

N-(tert-butoxycarbonyl)-3-(phenylmethyl)-L-histidine, methyl ester (109013-56-1) → 3-(phenylmethyl)-L-histidine, dihydrochloride (109013-61-8)

Guidance literature:

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

DOI:10.1055/s-1987-27828

Reference yield:

(R)-3-(3-Benzyl-3H-imidazol-4-yl)-2-tert-butoxycarbonylamino-propionic acid methyl ester (109013-56-1) → (R)-2-Amino-3-(3-benzyl-3H-imidazol-4-yl)-propionic acid; hydrochloride (109013-61-8)

Guidance literature:

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

DOI:10.1021/jm00115a014

Reference yield:

benzyl triflate (17674-16-7) → (R)-2-Amino-3-(3-benzyl-3H-imidazol-4-yl)-propionic acid; hydrochloride (109013-61-8)

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: 6 N HCl / methanol / 1.5 h / Heating

With hydrogenchloride; In methanol;

DOI:10.1021/jm00115a014

upstream raw materials:

(R)-3-(3-Benzyl-3H-imidazol-4-yl)-2-tert-butoxycarbonylamino-propionic acid methyl ester

benzyl triflate

Boc-D-His(N^τ-Boc)-OMe

N-(tert-butoxycarbonyl)-3-(phenylmethyl)-L-histidine, methyl ester

Downstream raw materials:

(R)-1-Benzyl-5-diphenylacetyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine-6-carboxylic acid methyl ester

(R)-1-Benzyl-5-diphenylacetyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine-6-carboxylic acid

(R)-1-Benzyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine-6-carboxylic acid methyl ester

3-benzyl-L-histidine

Refernces

• 1、 Hodges, John C.. "Regiospecific Synthesis of 3-Substituted L-Histidines". . p. 20 - 24. Retrieved 2007/10/02.