(R)-N-Boc-3-Amino-3-phenylpropanoic acid

Base Information

• Chemical Name: (R)-N-Boc-3-Amino-3-phenylpropanoic acid
• CAS No.: 161024-80-2
• Molecular Formula: C14H19NO4
• Molecular Weight: 265.309
• Hs Code.: 29242990
• DSSTox Substance ID: DTXSID50426539
• Nikkaji Number: J1.917.738F
• Wikidata: Q72448357
• Mol file: 161024-80-2.mol

Synonyms:161024-80-2;(R)-N-Boc-3-Amino-3-phenylpropanoic acid;(R)-3-((tert-Butoxycarbonyl)amino)-3-phenylpropanoic acid;(R)-3-(Boc-amino)-3-phenylpropionic acid;Boc-(R)-3-amino-3-phenylpropionic acid;(3R)-3-[(tert-butoxycarbonyl)amino]-3-phenylpropanoic acid;(3R)-3-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoic acid;MFCD01320859;Boc-beta-Phe-OH;(R)-3-(BOC-AMINO)-3-PHENYLPROPANOIC ACID;Boc-beta-L-Phe-OH;boc-beta-phenylalanine;Boc-Phg-(C#CH2)OH;BOC-(R)-ss-phenylalanine;BOC-(R)-PHENYLALANINE;SCHEMBL348499;(R)-3-((tert-Butoxycarbonyl)amino)-3-phenylpropanoicacid;DTXSID50426539;JTNQFJPZRTURSI-LLVKDONJSA-N;AKOS013463259;Benzenepropanoic acid, beta-[[(1,1-dimethylethoxy)carbonyl]amino]-, (betaR)-;CS-W014592;AC-22059;AS-11231;Boc-beta-Phe-OH, >=96.0% (HPLC);EN300-135523;BOC-(R)-3-AMINO-3-PHENYLPROPANOIC ACID;J-009775;(3R)-N-(tert-Butoxycarbonyl)-3-phenyl-beta-alanine;(R)-3-(tert-butoxycarbonylamino)-3-phenylpropanoic acid;(R)-3-[(tert-butoxycarbonyl)amino]-3-phenylpropionic acid;(3R)-3-{[(tert-butoxy)carbonyl]amino}-3-phenylpropanoic acid;(R)-3-TERT-BUTOXYCARBONYLAMINO-3-PHENYL-PROPIONIC ACID

Chemical Property of (R)-N-Boc-3-Amino-3-phenylpropanoic acid

Chemical Property:

• Appearance/Colour: white powder
• Vapor Pressure: 6.42E-08mmHg at 25°C
• Melting Point: 123.4 °C
• Refractive Index: 1.527
• Boiling Point: 423.2 °C at 760 mmHg
• PKA: 4.32±0.10(Predicted)
• Flash Point: 209.8 °C
• PSA: 75.63000
• Density: 1.158 g/cm³
• LogP: 3.11800
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 265.13140809
• Heavy Atom Count: 19
• Complexity: 316

Purity/Quality:

98%,99%, ^*data from raw suppliers

Boc-L-beta-phenylalanine ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(CC(=O)O)C1=CC=CC=C1
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@H](CC(=O)O)C1=CC=CC=C1

Technology Process of (R)-N-Boc-3-Amino-3-phenylpropanoic acid

There total 15 articles about (R)-N-Boc-3-Amino-3-phenylpropanoic 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: 100.0%

C14H17NO4 → (R)-3-((tert-butoxycarbonyl)amino)-3-phenylpropanoic acid (161024-80-2)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In ethyl acetate; at 20 ℃; for 20h; under 30402 Torr;

DOI:10.1021/acs.orglett.0c04196

Reference yield: 95.0%

di-tert-butyl dicarbonate (24424-99-5) + (R)-3-phenyl-3-aminopropionic acid (614-19-7,3646-50-2,13921-90-9,40856-44-8) → (R)-3-((tert-butoxycarbonyl)amino)-3-phenylpropanoic acid (161024-80-2)

Guidance literature:

With sodium carbonate; In acetone; at 0 ℃; for 2h;

DOI:10.1016/S0960-894X(00)00562-X

Reference yield: 80.0%

[(R)-3-Oxo-1-phenyl-3-((1R,2R,4R)-1,7,7-trimethyl-2-trimethylsilanyloxy-bicyclo[2.2.1]hept-2-yl)-propyl]-carbamic acid tert-butyl ester → (R)-3-((tert-butoxycarbonyl)amino)-3-phenylpropanoic acid (161024-80-2)

Guidance literature:

With ammonium cerium(IV) nitrate; In acetonitrile; at 0 ℃; for 16h;

DOI:10.1002/(SICI)1521-3773(20000317)39:6<1063::AID-ANIE1063>3.0.CO;2-Y

upstream raw materials:

di-tert-butyl dicarbonate

(R)-3-phenyl-3-aminopropionic acid

(S)-2-(tert-butoxycarbonylaminophenylmethyl)malonic acid dibenzyl ester

tert-butyl benzylidenecarbamate

Downstream raw materials:

(R)-prop-2-ynyl 3-(tert-butoxycarbonylamino)-3-phenyl-propanoate

Refernces

• 1、 Zhou, Shengbin,Wang, Jiang,Chen, Xia,Acena, Jose Luis,Soloshonok, Vadim A.,Liu, Hong. "Chemical kinetic resolution of unprotected β-substituted β-amino acids using recyclable chiral ligands". supporting information. p. 7883 - 7886. Retrieved 2014/08/05.
• 2、 Li, Yi,Wang, Wenfu,Huang, Yumian,Zou, Qianwen,Zheng, Guojun. "Asymmetric biocatalysis of S-3-amino-3-phenylpropionic acid with new isolated Methylobacterium Y1-6". . p. 1674 - 1678. Retrieved 2013/11/19.