Methyl 2-tert-butyloxycarbonylaminoacrylate

Base Information

• Chemical Name: Methyl 2-tert-butyloxycarbonylaminoacrylate
• CAS No.: 55477-80-0
• Molecular Formula: C9H15NO4
• Molecular Weight: 201.222
• DSSTox Substance ID: DTXSID70448798
• Nikkaji Number: J531.569G
• Wikidata: Q72490901
• Mol file: 55477-80-0.mol

Synonyms:55477-80-0;Methyl 2-tert-butyloxycarbonylaminoacrylate;2-TERT-BUTOXYCARBONYLAMINO-ACRYLIC ACID METHYL ESTER;Methyl 2-[(2-methylpropan-2-yl)oxycarbonylamino]prop-2-enoate;methyl 2-(tert-butoxycarbonylamino)prop-2-enoate;methyl 2-{[(tert-butoxy)carbonyl]amino}prop-2-enoate;2-tert-Butoxycarbonylaminoacrylic acid methyl ester;methyl 2-[(tert-butoxycarbonyl)amino]prop-2-enoate;MFCD03840371;methyl 2-(tert-butoxycarbonylamino)acrylate;methyl 2-[(tert-butoxycarbonyl)amino]acrylate;Boc-dehydro-alanine methyl ester;Boc-deltaAla-OMe;2-(Boc-amino)-2-propenoic acid methyl ester;2-tert-Butoxycarbonylamino-acrylicacidmethylester;METHYL 2-TERT-BUTOXYCARBONYLAMINOACRYLATE;methyl 2-(boc-amino)acrylate;SCHEMBL295520;2-(tert-Butoxycarbonylamino)acrylic acid methyl ester;DTXSID70448798;MGBHVVGQPZDMHA-UHFFFAOYSA-N;2-tert-Butoxycarbonylamino-acrylic;AMY19771;AKOS015850913;DS-12038;Methyl2-tert-butyloxycarbonylaminoacrylate;CS-0014186;FT-0650967;A830664;N-(tert-butoxycarbonyl)dehydroalanine methyl ester;J-522063;N-(tert-Butyloxycarbonyl)-dehydroalanine methyl ester;Methyl 2-({[(2-methyl-2-propanyl)oxy]carbonyl}amino)acrylate;2-[[(1,1-dimethylethoxy)carbonyl]amino]-2-propenoic acid, methyl ester;2-[[(2-methylpropan-2-yl)oxy-oxomethyl]amino]-2-propenoic acid methyl ester

Chemical Property of Methyl 2-tert-butyloxycarbonylaminoacrylate

Chemical Property:

• Vapor Pressure: 0.009mmHg at 25°C
• Refractive Index: 1.449
• Boiling Point: 265.285 °C at 760 mmHg
• PKA: 9.55±0.46(Predicted)
• Flash Point: 114.241 °C
• PSA: 64.63000
• Density: 1.071 g/cm³
• LogP: 1.58870
• Storage Temp.: 2-8°C
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 201.10010796
• Heavy Atom Count: 14
• Complexity: 252

Purity/Quality:

98%Min ^*data from raw suppliers

Methyl2-(tert-Butoxycarbonyl)acrylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(=C)C(=O)OC
• Uses: Protected Acrylic Acid.

Technology Process of Methyl 2-tert-butyloxycarbonylaminoacrylate

There total 32 articles about Methyl 2-tert-butyloxycarbonylaminoacrylate 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%

N-tert-butyloxycarbonyl-L-serine methyl ester (2766-43-0) → methyl 2-[(tert-butoxycarbonyl)amino]acrylate (55477-80-0) + N-(tert-butoxycarbonyl)-L-3-iodoalanine methyl ester (93267-04-0,170848-34-7,889670-02-4)

Guidance literature:

With 1H-imidazole; iodine; triphenylphosphine; In dichloromethane; at 0 - 20 ℃; for 4.5h; Inert atmosphere; Darkness;

DOI:10.15227/orgsyn.092.0103

Reference yield: 70.0%

N-(tert-butoxycarbonyl)-L-3-iodoalanine methyl ester (93267-04-0,170848-34-7,889670-02-4) → methyl 2-[(tert-butoxycarbonyl)amino]acrylate (55477-80-0) + (S)-2-tert-butoxycarbonylamino-3-phenyl-propionic acid methyl ester (51987-73-6)

Guidance literature:

In diethyl ether; at -10 ℃; for 5h;

DOI:10.1016/S0040-4039(01)81283-1

Reference yield: 67.0%

1,2,4-Triazole (288-88-0) + Bz(NO2)-ΔAla(N-Boc)-OMe → methyl 2-[(tert-butoxycarbonyl)amino]acrylate (55477-80-0) + Bz(NO2)-Ala[N-Boc-β-(1,2,4-triazol-1-yl)]-OMe

Guidance literature:

With potassium carbonate; In acetonitrile; at 20 ℃;

DOI:10.1039/b003353g

upstream raw materials:

N-tert-butyloxycarbonyl-L-serine methyl ester

methyllithium

methyl (2S)-2-[N-(t-butoxycarbonyl)amino]-3-(4-methylbenzenesulfonyl)-oxypropionate

N-(tert-butoxycarbonyl)-L-3-iodoalanine methyl ester

Downstream raw materials:

3-Benzylsulfanyl-2-tert-butoxycarbonylamino-propionic acid methyl ester

methyl 2-tert-butoxycarbonylamino-3-phenylpropanoate

(R)-3-((2-aminophenyl)thio)-2-((tert-butoxycarbonyl)amino)propanoic acid

Refernces

• 1、 Agelidis, Nektarios,Altevogt, Luca,Baro, Angelika,Bilitewski, Ursula,Bugdayci, Bakiye,Icik, Esra,Jolly, Anthony,L?ffler, Paul,Laschat, Sabine. "Synthesis and Biological Evaluation of a Library of AGE-Related Amino Acid Triazole Crosslinkers". supporting information. . Retrieved 2020/09/01.
• 2、 Boibessot, Thibaut,Bénimèlis, David,Jean, Marion,Benfodda, Zohra,Meffre, Patrick. "Synthesis of a Novel Rhizobitoxine-Like Triazole-Containing Amino Acid". . p. 2685 - 2688. Retrieved 2016/11/30.