N-[(Benzyloxy)carbonyl]norvaline

Base Information

• Chemical Name: N-[(Benzyloxy)carbonyl]norvaline
• CAS No.: 21691-43-0
• Molecular Formula: C13H17 N O4
• Molecular Weight: 251.282
• Hs Code.: 2924299090
• NSC Number: 97947
• Mol file: 21691-43-0.mol

Synonyms:21691-43-0;Z-DL-Nva-OH;N-Carbobenzoxy-DL-norvaline;N-[(Benzyloxy)carbonyl]norvaline;2-(phenylmethoxycarbonylamino)pentanoic acid;N-Cbz-dl-norvaline;N-CBZ-L-NORVALINE;DL-Norvaline, N-[(phenylmethoxy)carbonyl]-;Z-L-alpha-aminovaleric acid;Z-L-norvaline;Cbz-DL-norvaline;MFCD00063167;MFCD00136826;Z-DL-2-AMINOVALERIC ACID;NSC97947;2-{[(benzyloxy)carbonyl]amino}pentanoic acid;Carbobenzyloxy-dl-norvaline;NCIOpen2_006310;SCHEMBL329038;Norvaline, N-benzyl ester, DL-;N-[(Benzyloxy)carbonyl]norvaline #;MFCD00020434;NSC-97947;AKOS009159283;HY-W142126;2-(benzyloxycarbonylamino)pentanoic acid;AS-56328;SY023254;SY033677;CS-0201909;FT-0653574;FT-0659383;EN300-84284;Norvaline, N-carboxy-, N-benzyl ester, DL-;D89291;A815611;A826066;A878960;J-014235;N-Cbz-L-norvaline

Chemical Property of N-[(Benzyloxy)carbonyl]norvaline

Chemical Property:

• Vapor Pressure: 1.69E-08mmHg at 25°C
• Melting Point: 88 °C
• Boiling Point: 439.4°Cat760mmHg
• Flash Point: 219.6°C
• PSA: 75.63000
• Density: 1.184g/cm³
• LogP: 2.55700
• Solubility.: almost transparency in Methanol
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 251.11575802
• Heavy Atom Count: 18
• Complexity: 274

Purity/Quality:

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

Z-DL-norvaline ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCC(C(=O)O)NC(=O)OCC1=CC=CC=C1

Technology Process of N-[(Benzyloxy)carbonyl]norvaline

There total 4 articles about N-[(Benzyloxy)carbonyl]norvaline 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: 80.0%

2-aminopentanoic acid (760-78-1,498-18-0) + benzyl chloroformate (501-53-1,94274-21-2) → (R,S)-2-(N-benzyloxycarbonylamino)pentanoic acid (21691-43-0)

Guidance literature:

2-aminopentanoic acid; benzyl chloroformate; With sodium hydrogencarbonate; In water; at 0 - 20 ℃; for 24.75h; Inert atmosphere;

With hydrogenchloride; In water; pH=1;

DOI:10.1021/jm2004305

Reference yield:

N-benzyloxycarbonyl-DL-norvaline 2,2,2-trifluoroethyl ester (127862-67-3) → (S)-2-Benzyloxycarbonylamino-pentanoic acid (21691-43-0,21691-44-1,42918-89-8)

Guidance literature:

With sodium hydroxide; phosphate buffer; at 25 ℃; for 47h; Yield given; porcine pancreatic lipase, pH=7.0;

Reference yield:

2-aminopentanoic acid (760-78-1,498-18-0) → (R,S)-2-(N-benzyloxycarbonylamino)pentanoic acid (21691-43-0)

Guidance literature:

With sodium hydroxide; benzyl chloroformate;

upstream raw materials:

2-aminopentanoic acid

benzyl chloroformate

N-benzyloxycarbonyl-DL-norvaline 2,2,2-trifluoroethyl ester

Downstream raw materials:

N-CBz-D,L-norvaline dimethylamide

N-benzyloxycarbonyl-DL-norvaline 2,2,2-trifluoroethyl ester

benzyl N-[1-(dimethoxyphosphoryl)butyl]carbamate

{1-[N',N'-Bis-(2-chloro-ethyl)-hydrazinocarbonyl]-butyl}-carbamic acid benzyl ester

Refernces

• 1、 Miyazawa, Toshifumi,Mio, Motoe,Watanabe, Yuko,Yamada, Takashi. "Resolution of non-proteinogenic amino acids via microbial lipase-catalyzed enantioselective transesterification". . p. 219 - 224. Retrieved 2008/09/20.
• 2、 Oka, Takahiro,Yasusa, Takuya,Ando, Takashi,Watanabe, Mayumi,Yoneda, Fumio,Ishida, Toshimasa,Knoll, Joseph. "Enantioselective synthesis and absolute configuration of (-)-1-(benzofuran-2-yl)-2-propylaminopentane, ((-)-BPAP), a highly potent and selective catecholaminergic activity enhancer". . p. 1213 - 1219. Retrieved 2007/10/03.