(S)-2-tert-butoxycarbonylamino-4-azido-butanoic Acid Methyl Ester

Base Information

• Chemical Name: (S)-2-tert-butoxycarbonylamino-4-azido-butanoic Acid Methyl Ester
• CAS No.: 359781-97-8
• Molecular Formula: C10H18 N4 O4
• Molecular Weight: 258.277
• Hs Code.: 2929909090
• DSSTox Substance ID: DTXSID20456287
• Nikkaji Number: J2.654.451C
• Wikidata: Q82278646
• Mol file: 359781-97-8.mol

Synonyms:359781-97-8;(2S)-N-Boc-2-amino-4-azido-butanoic Acid Methyl Ester;(S)-2-tert-butoxycarbonylamino-4-azido-butanoic Acid Methyl Ester;Methyl (2S)-4-azido-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoate;N-BOC-2-AMINO-4-AZIDO-BUTANOIC ACID METHYL ESTER;SCHEMBL17747019;DTXSID20456287;(2S)-4-Azido-2-[[(1,1-Dimethylethoxy)carbonyl]amino]butanoic Acid Methyl Ester;CS-0363200;F79636;Methyl (S)-4-azido-2-((tert-butoxycarbonyl)amino)butanoate;(S)-2-(tert-Butoxycarbonylamino)-4-azidobutyric acid methyl ester

Chemical Property of (S)-2-tert-butoxycarbonylamino-4-azido-butanoic Acid Methyl Ester

Chemical Property:

• Melting Point: 35-37oC
• PSA: 114.38000
• LogP: 1.59676
• Solubility.: Chloroform
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 8
• Exact Mass: 258.13280507
• Heavy Atom Count: 18
• Complexity: 344

Purity/Quality:

98.5% ^*data from raw suppliers

(2S)-N-Boc-2-amino-4-azido-butanoicAcidMethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(CCN=[N+]=[N-])C(=O)OC
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@@H](CCN=[N+]=[N-])C(=O)OC
• Uses: N-Boc-2-amino-4-azido-butanoic Acid Methyl Ester useful for the treatment of Alzheimer disease. Amino acid derivative useful for the treatment of Alzheimer's

Technology Process of (S)-2-tert-butoxycarbonylamino-4-azido-butanoic Acid Methyl Ester

There total 10 articles about (S)-2-tert-butoxycarbonylamino-4-azido-butanoic 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: 97.0%

methyl (2S)-2-(tert-butoxycarbonyl)amino-4-iodobutanoate (101650-14-0) → methyl 4-azido-2S-{[(1,1-dimethylethoxy)carbonyl]amino}butyrate (359781-97-8)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; at 90 ℃; for 2h;

DOI:10.1021/jo026257s

Reference yield: 89.0%

methyl (S)-4-hydroxy-2-((tert-butoxy)carbonylamino)-butyrate (120042-11-7,258351-86-9) → methyl 4-azido-2S-{[(1,1-dimethylethoxy)carbonyl]amino}butyrate (359781-97-8)

Guidance literature:

methyl (S)-4-hydroxy-2-((tert-butoxy)carbonylamino)-butyrate; With diphenyl phosphoryl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 18h;

With sodium azide; In N,N-dimethyl-formamide; at 60 ℃; for 10h;

DOI:10.1016/j.tetlet.2014.06.036

Reference yield: 85.0%

dimethyl sulfate (77-78-1) + (S)-(+)-4-azido-2-((tert-butoxycarbonyl)amino)butanoic acid → methyl 4-azido-2S-{[(1,1-dimethylethoxy)carbonyl]amino}butyrate (359781-97-8)

Guidance literature:

With potassium carbonate; In acetone; at 55 ℃;

DOI:10.1021/acs.orglett.0c01950

upstream raw materials:

methyl (2S)-2-(tert-butoxycarbonyl)amino-4-iodobutanoate

(S)-2-amino-4-bromobutyric acid methyl ester

methyl (2S)-4-bromo-2-[(tert-butoxycarbonyl)amino]butanoate

methyl (S)-4-hydroxy-2-((tert-butoxy)carbonylamino)-butyrate

Refernces

• 1、 Gupta, Manoj Kumar,Madhanagopal, Bharath Raj,Ganesh, Krishna N.. "Peptide Nucleic Acid with Double Face: Homothymine-Homocytosine Bimodal Cα-PNA (bm-Cα-PNA) Forms a Double Duplex of the bm-PNA2:DNA Triplex". supporting information. p. 414 - 428. Retrieved 2020/12/22.
• 2、 Kawazoe, Yoshinori,Tanaka, Yoko,Omura, Sachikazu,Uemura, Daisuke. "Design, synthesis, and evaluation, derivatives of the fat-accumulation inhibitor ternatin: Toward ternatin molecular probes". supporting information. p. 4445 - 4447. Retrieved 2014/08/05.