N-Benzyl (S)-β-(CarboxyaMino)-hydrocinnaMic Acid Methyl Ester

Base Information

• Chemical Name: N-Benzyl (S)-β-(CarboxyaMino)-hydrocinnaMic Acid Methyl Ester
• CAS No.: 32975-59-0
• Molecular Formula: C18H19NO4
• Molecular Weight: 313.353
• Mol file: 32975-59-0.mol

Synonyms:(S)-|A-[[(Phenylmethoxy)carbonyl]amino]-benzenepropanoic Acid Methyl Ester;N-Benzyl (S)-|A-(Carboxyamino)-hydrocinnamic Acid Methyl Ester;

Chemical Property of N-Benzyl (S)-β-(CarboxyaMino)-hydrocinnaMic Acid Methyl Ester

Chemical Property:

• Melting Point: 58-60 °C
• Boiling Point: 473.3±45.0 °C(Predicted)
• PKA: 11.00±0.46(Predicted)
• PSA: 68.12000
• Density: 1.180±0.06 g/cm3(Predicted)
• LogP: 3.42160
• Solubility.: Dichloromethane, Methanol

Purity/Quality:

98% ^*data from raw suppliers

(S)-β-[[(Phenylmethoxy)carbonyl]amino]-benzenepropanoicAcidMethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (S)-β-[[(Phenylmethoxy)carbonyl]amino]-benzenepropanoic Acid Methyl Ester (cas# 32975-59-0) is a compound useful in organic synthesis.

Technology Process of N-Benzyl (S)-β-(CarboxyaMino)-hydrocinnaMic Acid Methyl Ester

There total 21 articles about N-Benzyl (S)-β-(CarboxyaMino)-hydrocinnaMic Acid Methyl Ester 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: 91.0%

methanol (67-56-1) + (R)-(-)-α-benzyloxycarbonylaminobenzyldiazomethyl ketone (32975-58-9) → methyl (S)-β-[[(phenylmethoxy)carbonyl]amino]-benzenepropanoate (32975-59-0)

Guidance literature:

With silver benzoate; triethylamine; for 3h;

Reference yield: 54.0%

methanol (67-56-1) + O-p-toluenesulfonyl benzyloxyhydroxamate (64420-86-6) + 3-phenyl-propenal (104-55-2) → methyl (S)-β-[[(phenylmethoxy)carbonyl]amino]-benzenepropanoate (32975-59-0)

Guidance literature:

O-p-toluenesulfonyl benzyloxyhydroxamate; 3-phenyl-propenal; With (2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine; sodium acetate; In chloroform; at 20 ℃; for 0.5h;

methanol; With 2-pentafluorophenyl-6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazol-2-ium tetrafluoroborate; In chloroform; at 20 ℃; for 16h; optical yield given as %ee; enantioselective reaction;

DOI:10.1002/chem.201100042

Reference yield:

(3S)-methyl 3-amino-3-phenylpropanoate (37088-66-7) + benzyl chloroformate (501-53-1,94274-21-2) → methyl (S)-β-[[(phenylmethoxy)carbonyl]amino]-benzenepropanoate (32975-59-0)

Guidance literature:

With pyridine; In dichloromethane; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1002/adsc.200900676

upstream raw materials:

methanol

(R)-(-)-α-benzyloxycarbonylaminobenzyldiazomethyl ketone

(R)-phenylglycine

Z-D-phenylglycine

Downstream raw materials:

(S)-(-)-β-Phenyl-β-alanine hydrochloride

(S)-benzyl [5-(1,3-dioxoisoindolin-2-yl)-3-oxo-1-phenylpentyl]carbamate

(S)-benzyl [2-(2-(2-(1,3-dioxoisoindolin-2-yl)ethyl)-1,3-dioxan-2-yl)-1-phenylethyl]carbamate

(S)-benzyl [2-(2-(2-aminoethyl)-1,3-dioxan-2-yl)-1-phenylethyl]carbamate

Refernces

• 1、 Annibaletto, Julien,Martzel, Thomas,Levacher, Vincent,Oudeyer, Sylvain,Brière, Jean-Fran?ois. "Multicomponent Catalytic Enantioselective Synthesis of Isoxazolidin-5-Ones". . p. 4447 - 4451. Retrieved 2021/08/09.
• 2、 Abrunhosa-Thomas, Isabelle,Plas, Aurelie,Vogrig, Alexandre,Kandepedu, Nishanth,Chalard, Pierre,Troin, Yves. "Access to 2,6-disubstituted piperidines: Control of the diastereoselectivity, scope, and limitations. applications to the stereoselective synthesis of (-)-solenopsine A and alkaloid (+)-241D". . p. 2511 - 2526. Retrieved 2013/04/24.