(R)-2-(((Benzyloxy)carbonyl)amino)butanoic acid

Base Information

• Chemical Name: (R)-2-(((Benzyloxy)carbonyl)amino)butanoic acid
• CAS No.: 2900-20-1
• Molecular Formula: C12H15 N O4
• Molecular Weight: 237.255
• Hs Code.: 2924299090
• DSSTox Substance ID: DTXSID50448115
• Nikkaji Number: J57.601H
• Wikidata: Q82267058
• Mol file: 2900-20-1.mol

Synonyms:2900-20-1;Z-D-Abu-OH;(R)-2-(((Benzyloxy)carbonyl)amino)butanoic acid;N-Alpha-carbobenzoxy-d-2-aminobutanoic acid;Butanoic acid, 2-[[(phenylmethoxy)carbonyl]amino]-, (2R)-;(R)-2-(Cbz-amino)butyric Acid;(2R)-2-(phenylmethoxycarbonylamino)butanoic acid;(2R)-2-{[(benzyloxy)carbonyl]amino}butanoic acid;Z-D-2Abu-OH;SCHEMBL2895983;DTXSID50448115;MFCD00136772;AKOS015156909;DS-16196;CARBOBENZYLOXY-D-2-AMINOBUTYRIC ACID;CARBOBENZYLOXY-L-2-AMINOBUTYRIC ACID;(R)-2-(benzyloxycarbonylamino)butanoic acid;CS-0041677;(R)-2-[(Benzyloxy)carbonylamino]butyric acid;EN300-121332;A876559;(R)-N-alpha-BenZyloxycarbonal-2-aminobutanoic acid (CbZ-D-2Abu-OH)

Chemical Property of (R)-2-(((Benzyloxy)carbonyl)amino)butanoic acid

Chemical Property:

• Boiling Point: 430.3°Cat760mmHg
• Flash Point: 214°C
• PSA: 75.63000
• Density: 1.213g/cm³
• LogP: 2.16690
• Storage Temp.: 2-8°C
• XLogP3: 2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 237.10010796
• Heavy Atom Count: 17
• Complexity: 261

Purity/Quality:

99.3% ^*data from raw suppliers

Z-D-2Abu-OH ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(C(=O)O)NC(=O)OCC1=CC=CC=C1
• Isomeric SMILES: CC[C@H](C(=O)O)NC(=O)OCC1=CC=CC=C1

Technology Process of (R)-2-(((Benzyloxy)carbonyl)amino)butanoic acid

There total 17 articles about (R)-2-(((Benzyloxy)carbonyl)amino)butanoic 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: 82.0%

L-2-aminobutyric acid (1492-24-6) + benzyl chloroformate (501-53-1,94274-21-2) → (S)-2-(((benzyloxy)carbonyl)amino)butanoic acid (42918-86-5,1145-79-5,2900-20-1,20395-87-3)

Guidance literature:

With sodium hydrogencarbonate; In water; for 20h; Ambient temperature;

DOI:10.1248/cpb.42.1927

Reference yield: 76.0%

ethanol (64-17-5) + 2-(N-benzyloxycarbonylamino)butyric acid (20395-87-3) → (2R)-2-[(phenylmethoxy)carbonyl]aminobutanoic acid (2900-20-1) + L-Z-2-aminoBu-OEt (92278-20-1)

Guidance literature:

With citrate buffer; DL-cysteine hydrochloride; papain; at 50 ℃; for 24h;

Reference yield:

N-(benzyloxycarbonyl)-L-glutamic acid anhydride (4124-76-9) → 4-(benzyloxycarbonylamino)butyric acid (5105-78-2) + (S)-2-(((benzyloxy)carbonyl)amino)butanoic acid (42918-86-5,1145-79-5,2900-20-1,20395-87-3)

Guidance literature:

With hydrogenchloride; bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; 2.9-dimethyl-1,10-phenanthroline; Yield given. Multistep reaction. Yields of byproduct given; 1.) THF, reflux, 2.5h.;

DOI:10.1016/S0040-4039(00)97733-5

upstream raw materials:

L-2-aminobutyric acid

benzyl chloroformate

((S)-2-Oxo-oxetan-3-yl)-carbamic acid benzyl ester

methyllithium

Downstream raw materials:

N-((S)-2-amino-butyryl)-L-tyrosine ethyl ester; hydrochloride

N-((S)-2-benzyloxycarbonylamino-butyryl)-glycine ethyl ester

Z-Abu-Sar-(Me)Leu-Val-(Me)Leu-Ala-D-Ala-(Me)Leu-(Me)Leu-(Me)Val-OBut

[(1S)-1-(hydroxymethyl)propyl]carbamic acid benzyl ester

Refernces

• 1、 -. "Oxazolidin-2-one-Pyrimidine Derivatives". Paragraph 0230. . Retrieved 2014/05/20.
• 2、 Ueda, Masafumi,Miyabe, Hideto,Teramachi, Masako,Miyata, Okiko,Naito, Takeaki. "Diastereoselective intermolecular radical addition to nitrones". . p. 6653 - 6660. Retrieved 2007/10/03.