(R)-2-Amino-3-(4-hydroxyphenyl)propanamide hydrochloride

Base Information

• Chemical Name: (R)-2-Amino-3-(4-hydroxyphenyl)propanamide hydrochloride
• CAS No.: 117888-79-6
• Molecular Formula: C₉H₁₂N₂O₂*ClH
• Molecular Weight: 216.667
• European Community (EC) Number: 836-937-4
• DSSTox Substance ID: DTXSID00704854
• Mol file: 117888-79-6.mol

Synonyms:117888-79-6;H-D-Tyr-NH2.HCl;(R)-2-Amino-3-(4-hydroxyphenyl)propanamide hydrochloride;D-Tyrosine amide hydrochloride;(2R)-2-amino-3-(4-hydroxyphenyl)propanamide;hydrochloride;DTXSID00704854;MFCD03701462;AKOS016844327;BP-10564;D-Tyrosinamide--hydrogen chloride (1/1);CS-0309234;EN300-1703712;H-D-Tyr-NH2 inverted exclamation mark currencyHCl;Z3211890270;S-117888-79-6;(2R)-2-AMINO-3-(4-HYDROXYPHENYL)PROPANAMIDE HYDROCHLORIDE

Chemical Property of (R)-2-Amino-3-(4-hydroxyphenyl)propanamide hydrochloride

Chemical Property:

• Storage Temp.: Sealed in dry,Room Temperature
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 216.0665554
• Heavy Atom Count: 14
• Complexity: 177

Purity/Quality:

99% ^*data from raw suppliers

H-D-Tyr-NH2Hydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1CC(C(=O)N)N)O.Cl
• Isomeric SMILES: C1=CC(=CC=C1C[C@H](C(=O)N)N)O.Cl

Technology Process of (R)-2-Amino-3-(4-hydroxyphenyl)propanamide hydrochloride

There total 4 articles about (R)-2-Amino-3-(4-hydroxyphenyl)propanamide hydrochloride 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%

tert-butyl (S)-(1-amino-3-(4-hydroxyphenyl)-1-oxopropan-2-yl)carbamate (83351-75-1) → (S)-2-amino-3-(4-hydroxyphenyl)propanamide hydrochloride (53559-18-5,117888-79-6,117888-80-9,2442565-30-0)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; methanol; at 0 - 20 ℃; for 16h;

DOI:10.1021/acs.jmedchem.8b01466

Reference yield:

L-tyrosine hydrochloride (16870-43-2,282733-43-1) → (S)-2-amino-3-(4-hydroxyphenyl)propanamide hydrochloride (53559-18-5,117888-79-6,117888-80-9,2442565-30-0)

Guidance literature:

With hexamethylphosphorous triamide dichloride; ammonia; In dichloromethane; 1) 30 min, -20 deg C, 2) 4 h, r.t.;

Reference yield:

Boc-Tyr-OH (3978-80-1) → (S)-2-amino-3-(4-hydroxyphenyl)propanamide hydrochloride (53559-18-5,117888-79-6,117888-80-9,2442565-30-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: isobutyl chloroformate; 4-methyl-morpholine / dichloromethane / 0.83 h / 0 °C

1.2: 16.08 h / 0 - 25 °C

2.1: hydrogenchloride / 1,4-dioxane; methanol / 16 h / 0 - 20 °C

With 4-methyl-morpholine; hydrogenchloride; isobutyl chloroformate; In 1,4-dioxane; methanol; dichloromethane;

DOI:10.1021/acs.jmedchem.8b01466

upstream raw materials:

L-tyrosine hydrochloride

Boc-Tyr-OH

tert-butyl (S)-(1-amino-3-(4-hydroxyphenyl)-1-oxopropan-2-yl)carbamate

L-tyrosine

Downstream raw materials:

(S)-2-tert-Butoxycarbonylamino-propionic acid (S)-1-[(S)-1-carbamoyl-2-(4-hydroxy-phenyl)-ethylcarbamoyl]-2-methyl-propyl ester

Boc-Tyr-D-Arg(Tos)-Phe-Gly-Tyr-NH₂

benzyl ((S)-1-(((S)-1-amino-3-(4-hydroxyphenyl)-1-oxopropan-2-yl)amino)-4-methyl-1-oxopentan-2-yl)carbamate

NPS-Phe-Tyr-NH₂

Refernces

• 1、 Appel, Rolf,Hiester, Ernst. "Dichlorotris(dimethylamino)phosphorane as a Dehydratisation Reagent for the Preparation of N-Protected Amino Acid Amides". . p. 2037 - 2040. Retrieved 2007/10/02.