Phenylalanine, b-hydroxy-, methyl ester, hydrochloride

Base Information

• Chemical Name: Phenylalanine, b-hydroxy-, methyl ester, hydrochloride
• CAS No.: 80182-99-6
• Molecular Formula: C10H13NO3.ClH
• Molecular Weight: 231.679
• Mol file: 80182-99-6.mol

Synonyms:

Chemical Property of Phenylalanine, b-hydroxy-, methyl ester, hydrochloride

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Phenylalanine, b-hydroxy-, methyl ester, hydrochloride

There total 5 articles about Phenylalanine, b-hydroxy-, methyl ester, 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: 97.0%

methanol (67-56-1) + Phenylserin (69-96-5) → β-hydroxyphenylalanine methyl ester hydrochloride (80182-99-6)

Guidance literature:

With thionyl chloride; at 41 ℃; for 1h;

DOI:10.1021/acs.biomac.5b01006

Reference yield:

methanol (67-56-1) + (2RS,3RS)-2-amino-3-hydroxy-3-phenyl-propionic acid (69-96-5,1078-17-7,2584-74-9,2584-75-0,6254-48-4,7352-06-9,7687-36-7,7695-56-9,32946-42-2,50897-27-3,68296-26-4,109120-55-0) → (2RS,3RS)-2-amino-3-hydroxy-3-phenyl-propionic acid methyl ester; hydrochloride (17193-41-8,17193-42-9,32926-34-4,39687-93-9,80182-99-6,99723-37-2,104320-72-1)

Guidance literature:

With thionyl chloride; Ambient temperature;

Reference yield:

α-Phenylacyl amino acid methyl ester hydrochloride (38061-23-3,81202-39-3) → C10H13NO3*ClH + (2RS,3RS)-2-amino-3-hydroxy-3-phenyl-propionic acid methyl ester; hydrochloride (17193-41-8,17193-42-9,32926-34-4,39687-93-9,80182-99-6,99723-37-2,104320-72-1)

Guidance literature:

With dichloro(benzene)ruthenium(II) dimer; hydrogen; (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine); In methanol; at 50 ℃; for 48h; under 76005.1 Torr; optical yield given as %de; diastereoselective reaction;

DOI:10.1016/j.tetasy.2008.12.024

upstream raw materials:

methanol

(2RS,3RS)-2-amino-3-hydroxy-3-phenyl-propionic acid

α-Phenylacyl amino acid methyl ester hydrochloride

Phenylserin

Downstream raw materials:

(2RS,3RS)-2-amino-3-hydroxy-3-phenyl-propionic acid

methyl (Z)-N-(Boc-valyl)dehydrophenylalaninate

methyl (S,Z)-2-(2-((tert-butoxycarbonyl)amino)propanamido)-3-phenylacrylate

Refernces

• 1、 Echeverria, Pierre-Georges,Cornil, Johan,Férard, Charlène,Guérinot, Amandine,Cossy, Janine,Phansavath, Phannarath,Ratovelomanana-Vidal, Virginie. "Asymmetric transfer hydrogenation of α-amino β-keto ester hydrochlorides through dynamic kinetic resolution". . p. 56815 - 56819. Retrieved 2015/07/15.
• 2、 Makino, Kazuishi,Goto, Takayuki,Hiroki, Yasuhiro,Hamada, Yasumasa. "Direct anti-selective asymmetric hydrogenation of α-amino-β-keto esters through dynamic kinetic resolution using Ru-axially chiral phosphine catalysts-stereoselective synthesis of anti-β-hydroxy-α-amino acids". experimental part. p. 2816 - 2828. Retrieved 2009/06/28.