(S)-3-BIPHENYL-3-YL-2-TERT-BUTOXYCARBONYLAMINO-PROPIONIC ACID

Base Information

• Chemical Name: (S)-3-BIPHENYL-3-YL-2-TERT-BUTOXYCARBONYLAMINO-PROPIONIC ACID
• CAS No.: 608528-91-2
• Molecular Formula: C₂₀H₂₃NO₄
• Molecular Weight: 341.407
• Hs Code.: 2924297099
• Mol file: 608528-91-2.mol

Synonyms:(S)-3-BIPHENYL-3-YL-2-TERT-BUTOXYCARBONYLAMINO-PROPIONIC ACID;BOC-L-2-AMINO-3-BIPHENYL-3-YL-PROPIONIC ACID;Boc-(S)-2-AMino-3-biphenyl-3-yl-propionic acid

Chemical Property of (S)-3-BIPHENYL-3-YL-2-TERT-BUTOXYCARBONYLAMINO-PROPIONIC ACID

Chemical Property:

• PSA: 75.63000
• LogP: 4.26490

Purity/Quality:

98%min ^*data from raw suppliers

Boc-(S)-2-Amino-3-biphenyl-3-yl-propionicacid 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (S)-3-BIPHENYL-3-YL-2-TERT-BUTOXYCARBONYLAMINO-PROPIONIC ACID

There total 4 articles about (S)-3-BIPHENYL-3-YL-2-TERT-BUTOXYCARBONYLAMINO-PROPIONIC ACID 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:

(2S)-3-(3-bromophenyl)-2-[(tert-butoxycarbonyl)amino]propanoic acid (82278-73-7) + phenylboronic acid (98-80-6) → (S)-3-Biphenyl-3-yl-2-tert-butoxycarbonylamino-propionic acid (608528-91-2,1259986-44-1)

Guidance literature:

With dichloro bis(acetonitrile) palladium(II); In tetrahydrofuran; water; at 120 ℃; for 0.333333h; Microwave irradiation;

DOI:10.1039/c6cy00855k

Reference yield:

3-bromocinnamic acid (14473-91-7,20595-41-9,32862-97-8) → (S)-3-Biphenyl-3-yl-2-tert-butoxycarbonylamino-propionic acid (608528-91-2,1259986-44-1)

Guidance literature:

Multi-step reaction with 3 steps

1: recombinant cyanobacterium Anabaena variabilis phenylalanine ammonia lyase; ammonium carbamate / water / 24 h / 30 °C / Enzymatic reaction

2: caesium carbonate / water; tetrahydrofuran / 0.33 h / 90 °C / Microwave irradiation

3: dichloro bis(acetonitrile) palladium(II) / water; tetrahydrofuran / 0.33 h / 120 °C / Microwave irradiation

With dichloro bis(acetonitrile) palladium(II); recombinant cyanobacterium Anabaena variabilis phenylalanine ammonia lyase; ammonium carbamate; caesium carbonate; In tetrahydrofuran; water; 3: |Suzuki-Miyaura Coupling;

DOI:10.1039/c6cy00855k

Reference yield:

(S)-2-((tert-butoxycarbonyl)amino)-3-(3-iodophenyl)propanoic acid (273221-75-3) → (S)-3-Biphenyl-3-yl-2-tert-butoxycarbonylamino-propionic acid (608528-91-2,1259986-44-1)

Guidance literature:

Multi-step reaction with 3 steps

1: potassium carbonate / acetone / Reflux

2: sodium carbonate; tris-(o-tolyl)phosphine; palladium diacetate / water; 1,2-dimethoxyethane / 3 h / 80 °C / Inert atmosphere

3: palladium on activated charcoal; hydrogen

With palladium on activated charcoal; hydrogen; palladium diacetate; sodium carbonate; potassium carbonate; tris-(o-tolyl)phosphine; In 1,2-dimethoxyethane; water; acetone; 2: |Suzuki Coupling;

DOI:10.1016/j.bmcl.2016.04.023

upstream raw materials:

(S)-2-((tert-butoxycarbonyl)amino)-3-(3-iodophenyl)propanoic acid

benzyl (S)-3-([1,1’-biphenyl]-3-yl)-2-((tert-butoxycarbonyl)amino)propanoate

3-bromocinnamic acid

(2S)-3-(3-bromophenyl)-2-[(tert-butoxycarbonyl)amino]propanoic acid

Refernces

• 1、 Weise, Nicholas J.,Ahmed, Syed T.,Parmeggiani, Fabio,Siirola, Elina,Pushpanath, Ahir,Schell, Ursula,Turner, Nicholas J.. "Intensified biocatalytic production of enantiomerically pure halophenylalanines from acrylic acids using ammonium carbamate as the ammonia source". . p. 4086 - 4089. Retrieved 2016/07/06.