Ethyl N-(tert-butoxycarbonyl)oxamate

Base Information

• Chemical Name: Ethyl N-(tert-butoxycarbonyl)oxamate
• CAS No.: 216959-34-1
• Molecular Formula: C9H15NO5
• Molecular Weight: 217.222
• Hs Code.: 2924199090
• European Community (EC) Number: 625-040-1
• DSSTox Substance ID: DTXSID80369965
• Nikkaji Number: J990.200G
• Wikidata: Q82157262
• Mol file: 216959-34-1.mol

Synonyms:216959-34-1;Ethyl N-(tert-butoxycarbonyl)oxamate;Ethyl 2-((tert-butoxycarbonyl)amino)-2-oxoacetate;Ethyl N-Boc-oxamidate;ethyl 2-(tert-butoxycarbonylamino)-2-oxoacetate;ETHYL N-BOC-OXAMATE;ethyl 2-[(2-methylpropan-2-yl)oxycarbonylamino]-2-oxoacetate;ethyl 2-{[(tert-butoxy)carbonyl]amino}-2-oxoacetate;n-boc ethyl oxamate;ethyl 2-(tert-butoxycarbonylamino)-2-oxo-acetate;SCHEMBL1294994;DTXSID80369965;DSDQWJVXMDHQLK-UHFFFAOYSA-N;ethyln-(tert-butoxycarbonyl)oxamate;Acetic acid, [[(1,1-dimethylethoxy)carbonyl]amino]oxo-, ethyl ester;Ethyl N-Boc-oxamidate, >=97.0%;MFCD01631201;AKOS015915332;AC-6512;AS-38804;ethyl 2-(tert-butoxycarbonyl)-2-oxoacetate;A4662;CS-0089486;FT-0687223;EN300-316943;N-(tert-Butoxycarbonyl)oxamidic acid ethyl ester;Ethyl2-((tert-butoxycarbonyl)amino)-2-oxoacetate;J-014237;tert-butoxycarbonylamino-oxo-acetic acid ethyl ester

Chemical Property of Ethyl N-(tert-butoxycarbonyl)oxamate

Chemical Property:

• Appearance/Colour: Clear colorless to pale yellow liquid
• Melting Point: 115-120°C
• Refractive Index: n20/D 1.449
• Boiling Point: 132-136 °C (0.1 mmHg)
• PKA: 7.99±0.46(Predicted)
• PSA: 81.70000
• Density: 1.142g/cm³
• LogP: 0.99170
• Storage Temp.: −20°C
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 217.09502258
• Heavy Atom Count: 15
• Complexity: 266

Purity/Quality:

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

EthylN-(tert-Butoxycarbonyl)oxamate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi; Xn
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C(=O)NC(=O)OC(C)(C)C
• Uses: Ethyl N-(tert-Butoxycarbonyl)oxamate is used in preparation of halogenated-aminomethyl substituted pyrimidine and salt thereof as drug intermediate.

Technology Process of Ethyl N-(tert-butoxycarbonyl)oxamate

There total 2 articles about Ethyl N-(tert-butoxycarbonyl)oxamate 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: 100.0%

ethoxycarbonylcarbonyl isocyanate (66913-88-0) + tert-butyl alcohol (75-65-0) → ethyl 2-{[(tert-butoxy)carbonyl]amino}-2-oxoacetate (216959-34-1)

Guidance literature:

In toluene; at 40 ℃; for 0.25h;

DOI:10.1080/00397919908086430

Reference yield: 70.0%

oxalyl dichloride (79-37-8) + Ethyl oxamate (617-36-7) + tert-butyl alcohol (75-65-0) → ethyl 2-{[(tert-butoxy)carbonyl]amino}-2-oxoacetate (216959-34-1)

Guidance literature:

In 1,2-dichloro-ethane; toluene; Inert atmosphere;

DOI:10.1021/acs.joc.1c00918

Reference yield: 98.0%

ethyl 2-{[(tert-butoxy)carbonyl]amino}-2-oxoacetate (216959-34-1) + C96H96O12 → C132H148N4O28

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 20 ℃; for 12h;

DOI:10.1002/1521-3765(20001016)6:20<3797::AID-CHEM3797>3.0.CO;2-1

upstream raw materials:

ethoxycarbonylcarbonyl isocyanate

tert-butyl alcohol

oxalyl dichloride

Ethyl oxamate

Downstream raw materials:

[tert-butoxycarbonyl-(3-phenyl-allyl)-amino]-oxo-acetic acid ethyl ester

[tert-butoxycarbonyl-(1-phenyl-ethyl)-amino]-oxo-acetic acid ethyl ester

ethyl 2-tert-butoxycarbonyl-1,2-dihydroisoquinoline-3-carboxylate

({2-[4-(allyl-dimethyl-silanyl)-phenyl]-ethyl}-tert-butoxycarbonyl-amino)-oxo-acetic acid ethyl ester

Refernces

• 1、 Lee, Kangwon,Rouillard, Jean-Marie,Pham, Trinh,Gulari, Erdogan,Kim, Jinsang. "Signal-amplifying conjugated polymer-DNA hybrid chips". . p. 4667 - 4670. Retrieved 2008/02/08.
• 2、 Berree, Fabienne,Bazureau, Jean-Pierre,Michelot, Gwendal,Le Corre, Maurice. "N-Boc and N-Cbz ethyl oxamates: New Gabriel reagents". . p. 2685 - 2693. Retrieved 2007/10/03.