216959-34-1

Basic information

• Product Name: ETHYL N-(TERT-BUTOXYCARBONYL)OXAMATE
• Synonyms: ETHYL N-BOC-OXAMIDATE;ETHYL N-(TERT-BUTOXYCARBONYL)OXAMATE;TERT-BUTOXYCARBONYLAMINO-OXO-ACETIC ACID ETHYL ESTER;N-BOC ETHYL OXAMATE;Acetic acid, [[(1,1-dimethylethoxy)carbonyl]amino]oxo-, ethyl ester (9CI);Boc-Ox-Et;N-t-Butyloxycarbonylethyloxamate;N-TERT-BUTYLOXYCARBONYL ETHYL OXAMATE
• CAS NO: 216959-34-1
• Molecular Formula: C₉H₁₅NO₅
• Molecular Weight: 217.22
• Product Categories: N-BOC;Amine ProtectionProtection and Derivatization;Others;Peptide Synthesis;Protecting and Derivatizing Reagents;Specialty Synthesis
• Mol File: 216959-34-1.mol
• Article Data: 5

Chemical Properties

• Melting Point: 115-120°C
• Boiling Point: 132-136 °C (0.1 mmHg)
• Appearance: Clear colorless to pale yellow liquid
• Density: 1.142g/cm³
• Refractive Index: n20/D 1.449
• Storage Temp.: −20°C
• PKA: 7.99±0.46(Predicted)
• BRN: 8201747
• CAS DataBase Reference: ETHYL N-(TERT-BUTOXYCARBONYL)OXAMATE(CAS DataBase Reference)
• NIST Chemistry Reference: ETHYL N-(TERT-BUTOXYCARBONYL)OXAMATE(216959-34-1)
• EPA Substance Registry System: ETHYL N-(TERT-BUTOXYCARBONYL)OXAMATE(216959-34-1)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22
• Safety Statements: 26-36
• WGK Germany: 3
• F: 10
• Hazardous Substances Data: 216959-34-1(Hazardous Substances Data)

Usage

Description

ETHYL N-(TERT-BUTOXYCARBONYL)OXAMATE is a chemical compound that serves as a crucial intermediate in the synthesis of various pharmaceuticals. It is characterized by its clear colorless to pale yellow liquid appearance and plays a significant role in the development of new drugs.

Uses

Used in Pharmaceutical Industry:
ETHYL N-(TERT-BUTOXYCARBONYL)OXAMATE is used as a key intermediate in the preparation of halogenated-aminomethyl substituted pyrimidine and its salt. ETHYL N-(TERT-BUTOXYCARBONYL)OXAMATE is essential for the development of new drugs, particularly in the pharmaceutical industry, as it aids in the synthesis of various drug candidates with potential therapeutic applications.

InChI:InChI=1/C9H15NO5/c1-5-14-7(12)6(11)10-8(13)15-9(2,3)4/h5H2,1-4H3,(H,10,11,13)

Upstream product

• 66913-88-0 ethoxycarbonylcarbonyl isocyanate 
• 75-65-0 tert-butyl alcohol 
• 79-37-8 oxalyl dichloride 
• 617-36-7 Ethyl oxamate 

Downstream Products

• 216959-42-1 [tert-butoxycarbonyl-(3-phenyl-allyl)-amino]-oxo-acetic acid ethyl ester 
• 216959-44-3 [tert-butoxycarbonyl-(1-phenyl-ethyl)-amino]-oxo-acetic acid ethyl ester 
• 298209-94-6 ethyl 2-tert-butoxycarbonyl-1,2-dihydroisoquinoline-3-carboxylate 
• 288372-52-1 ({2-[4-(allyl-dimethyl-silanyl)-phenyl]-ethyl}-tert-butoxycarbonyl-amino)-oxo-acetic acid ethyl ester 
• 955039-25-5 (E)-N-t-butoxycarbonyl-N-(ethoxyoxoacetyl)-4-(tert-butyldiphenylsilanyloxy)-2-fluoro-2-butenylamine 
• 932403-99-1 tert-butyl 5,5'-(2,5-dibromo-1,4-phenylene)bis(oxy)bis(pentane-5,1-diyl)dicarbamate 
• 83948-54-3 tert-butyl (5-bromopentyl)carbamate 
• 86953-79-9 tert-butyl pyrrolidine-1-carboxylate 
• 164365-88-2 tert-butyl 4-bromobutylcarbamate 
• 38267-76-4 tert-butyl N-ethylcarbamate 
• 147169-48-0 (R,S)-N-(tert-butyloxycarbonyl)-α-methylbenzylamine 
• 193751-54-1 tert-butyl cyclopent-3-en-1-ylcarbamate 

Relevant articles and documents

N-Methyl Allylic Amines from Allylic Alcohols by Mitsunobu Substitution Using N-Boc Ethyl Oxamate

We report the practical, scalable synthesis of a range of N-methyl allylic amines. Primary and secondary allylic alcohols underwent a regioselective Mitsunobu reaction with readily accessible N-Boc ethyl oxamate to deliver the corresponding N-Boc allylic amines, including in enantiopure form via stereospecific substitution. Subsequent N-methylation and Boc deprotection without chromatography yielded the amine products as hydrochloride salts. This method solves the problem of converting commercially available alcohols into often volatile N-methyl allylic amines, many of which have limited commercial availability.

Convenient Synthesis of 3,4-methano-1,2,3,4-tetrahydroisoquinoline-3-carboxylic Acid and Its Derivatives as Doubly Constrained Nonproteinogenic Amino Acid Derivatives

Three strategies for the synthesis of the novel, doubly constrained, 3,4-methano-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid and its derivatives were evaluated. Only cyclocondensation of the mono(triphenyl)phosphonium salt derived from 1,2-bis(bromomethyl)benzene with N-alkoxycarbonyloxamates in 1,2-dimethoxyethane in the presence of potassium carbonate and subsequent cyclopropanation with dimethylsulfoxonium methylide in dimethyl sulfoxide furnished suitable O-and N-protected derivatives of 3,4-methano-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid in a convenient way. A detailed 2D DQF-COSY and 2D NOESY NMR analysis of the rotational isomerism of the latter bicyclic amino acid derivatives was performed. Various O- and N-protection protocols were worked out to afford access to a whole range of new derivatives of the title amino acid, suitable for peptide synthesis.

N-Boc ethyl oxamate: A new nitrogen nucleophile for use in Mitsunobu reactions

N-Boc ethyl oxamate can be directly coupled with primary and secondary alcohols under Mitsunobu conditions to afford various N-Boc mines after mild deprotection.