2-((tert-Butoxycarbonyl)amino)ethyl 4-methylbenzenesulfonate

Base Information

• Chemical Name: 2-((tert-Butoxycarbonyl)amino)ethyl 4-methylbenzenesulfonate
• CAS No.: 158690-56-3
• Molecular Formula: C14H21NO5S
• Molecular Weight: 315.39
• Hs Code.: 2924299090
• European Community (EC) Number: 815-937-8
• DSSTox Substance ID: DTXSID20444861
• Nikkaji Number: J2.128.417C
• Wikidata: Q72470424
• Mol file: 158690-56-3.mol

Synonyms:158690-56-3;2-((tert-Butoxycarbonyl)amino)ethyl 4-methylbenzenesulfonate;Tert-butyl n-[2-(tosyloxy)ethyl]carbamate;2-(tert-butoxycarbonylamino)ethyl 4-methylbenzenesulfonate;2-[(2-methylpropan-2-yl)oxycarbonylamino]ethyl 4-methylbenzenesulfonate;tert-butyl N-{2-[(4-methylbenzenesulfonyl)oxy]ethyl}carbamate;SCHEMBL791306;AMY4997;DTXSID20444861;OWNIGLWHXOENAA-UHFFFAOYSA-N;toluene-4-sulfonic acid 2-tert-butoxycarbonylamino-ethyl Ester;MFCD07776965;AKOS015909305;AS-54919;Tert-butyln-[2-(tosyloxy)Ethyl]carbamate;2-(Boc-amino)ethyl 4-methylbenzenesulfonate;2-(tert-Butyloxycarbonylamino)ethyl Tosylate;CS-0148612;FT-0650923;2-(tert-butyloxycarbonylamino)-ethyl tosylate;EN300-75497;W11059;2-tert-butoxycarbonylaminoethyl 4-toluenesulfonate;A855775;2-((tert-Butoxycarbonyl)amino)ethyl4-methylbenzenesulfonate;2-(tert-butoxy-carbonylamino)ethyl 4-methylbenzenesulfonate;2-[(tert-Butoxycarbonyl)amino]ethyl 4-methylbenzene-1-sulfonate;p-Toluenesulfonic acid 2-[(tert-butyloxycarbonyl)amino]ethyl ester;2-({[(1,1-dimethylethyl)oxy]carbonyl}amino)ethyl 4-methylbenzenesulfonate;Carbamic acid, N-[2-[[(4-methylphenyl)sulfonyl]oxy]ethyl]-, 1,1-dimethylethyl ester

Chemical Property of 2-((tert-Butoxycarbonyl)amino)ethyl 4-methylbenzenesulfonate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.514
• Boiling Point: 461.949 °C at 760 mmHg
• PKA: 11.71±0.46(Predicted)
• Flash Point: 233.179 °C
• PSA: 90.08000
• Density: 1.189 g/cm³
• LogP: 3.69670
• Storage Temp.: 2-8°C(protect from light)
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 7
• Exact Mass: 315.11404394
• Heavy Atom Count: 21
• Complexity: 427

Purity/Quality:

98%min ^*data from raw suppliers

2-(tert-Butoxycarbonylamino)ethyl 4-methylbenzenesulfonate 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)S(=O)(=O)OCCNC(=O)OC(C)(C)C

Technology Process of 2-((tert-Butoxycarbonyl)amino)ethyl 4-methylbenzenesulfonate

There total 5 articles about 2-((tert-Butoxycarbonyl)amino)ethyl 4-methylbenzenesulfonate 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: 92.0%

2-(N-tert-butoxycarbonylamino)ethanol (26690-80-2) + p-toluenesulfonyl chloride (98-59-9) → 2-(tert-butoxycarbonylamino)ethyl-4-methylbenzenesulfonate (158690-56-3)

Guidance literature:

With pyridine; In dichloromethane; at 0 ℃; for 18h;

DOI:10.1039/c2ob25258a

Reference yield: 78.0%

tert-butyl (2-hydroxyethyl)carbamate + p-toluenesulfonyl chloride (98-59-9) → 2-(tert-butoxycarbonylamino)ethyl-4-methylbenzenesulfonate (158690-56-3)

Guidance literature:

With triethylamine; In dichloromethane; at 25 ℃; for 16h;

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → 2-(tert-butoxycarbonylamino)ethyl-4-methylbenzenesulfonate (158690-56-3)

Guidance literature:

Multi-step reaction with 2 steps

1: Et₃N

2: pyridine

With pyridine; triethylamine;

DOI:10.1002/jlcr.538

upstream raw materials:

2-(N-tert-butoxycarbonylamino)ethanol

p-toluenesulfonyl chloride

di-tert-butyl dicarbonate

tert-butyldicarbonate

Downstream raw materials:

3-chloro-4-[2-[[(1,1-dimethylethoxy)carbonyl]-amino]-ethylthio]benzeneacetic acid methyl ester

{2-[(2-benzylsulfanyl-ethyl)-(toluene-4-sulfonyl)-amino]-ethyl}-carbamic acid tert-butyl ester

tert-butyl 2-azidoethylcarbamate

N-(tert-butoxycarbonyl)-2-(acetylthio)ethylamine

Refernces

• 1、 Cai, Wei-Yan,Chen, Yan-Jun,De, Ge-Jing,Hao, Dan-Li,Liu, Li,Ma, Hai,Sui, Feng,Xie, Ran,Yang, Mi-Yi,Yi, Hong,Zang, Chen,Zhao, Qing-He. "PH-responsive artesunate polymer prodrugs with enhanced ablation effect on rodent xenograft colon cancer". . p. 1771 - 1786. Retrieved 2020.
• 2、 McGouran, Joanna F.,Kramer, Holger B.,MacKeen, Mukram M.,Di Gleria, Katalin,Altun, Mikael,Kessler, Benedikt M.. "Fluorescence-based active site probes for profiling deubiquitinating enzymes". . p. 3379 - 3383. Retrieved 2012.
• 3、 -. "Preparation method of N-Boc-N-[2-(2-chloro-5-pyrimidinyl)ethyl] amine". Paragraph 0024-0027; 0032-0035. . Retrieved 2022/01/04.
• 4、 Aharoni, Hila,Albeck, Shira,Avram, Liat,Brandis, Alexander,Gabizon, Ronen,Gehrtz, Paul,Gurwicz, Neta,Herishanu, Yair,Katz, Ben-Zion,Livnah, Ella,London, Nir,Shorer, Yamit,Shraga, Amit,Shulman, Ziv,Unger, Tamar. "Erratum: Efficient Targeted Degradation via Reversible and Irreversible Covalent PROTACs (Journal American Chemical Society (2020) DOI: 10.1021/jacs.9b13907)". supporting information. p. 11316 - 11316. Retrieved 2020/07/28.