26690-80-2

Basic information

• Product Name: TERT-BUTYL N-(2-HYDROXYETHYL)CARBAMATE
• Synonyms: N-T-BUTOXYCARBONYL-2-AMINOETHANOL;N-T-BUTOXYCARBONYL-GLYCINOL;N-(TERT-BUTOXYCARBONYL)ETHANOLAMINE;N-(2-HYDROXYETHYL)CARBAMIC ACID TERT-BUTYL ESTER;N-(2-HYDROXYMETHYL)CARBAMIC ACID BENZYL ESTER;N-BOC-2-AMINOETHANOL;N-BOC-ETHANOLAMINE;N-BOC-AMINOETHANOL
• CAS NO: 26690-80-2
• Molecular Formula: C₇H₁₅NO₃
• Molecular Weight: 161.2
• EINECS: 1312995-182-4
• Product Categories: Miscellaneous Natural Products;Amino Acids;Amino Alcohols;Boc-Amino acid series;Amines;Miscellaneous Reagents
• Mol File: 26690-80-2.mol

Chemical Properties

• Boiling Point: 92℃/0.22mm
• Flash Point: >230 °F
• Appearance: clear, light yellow/viscous liquid
• Density: 1.042 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00112mmHg at 25°C
• Refractive Index: n20/D 1.449(lit.)
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Sparingly), Methanol (Slightly)
• PKA: 12.01±0.46(Predicted)
• Water Solubility: Soluble in water or 1% acetic acid. Soluble in ethyl acetate and methanol.
• BRN: 2353995
• CAS DataBase Reference: TERT-BUTYL N-(2-HYDROXYETHYL)CARBAMATE(CAS DataBase Reference)
• NIST Chemistry Reference: TERT-BUTYL N-(2-HYDROXYETHYL)CARBAMATE(26690-80-2)
• EPA Substance Registry System: TERT-BUTYL N-(2-HYDROXYETHYL)CARBAMATE(26690-80-2)

Safety Data

• Hazard Codes: T
• Statements: 25-37/38-41-36/37/38-23/24/25
• Safety Statements: 26-39-45-36/37/39-37/39
• RIDADR: UN 2810 6.1/PG 3
• WGK Germany: 3
• F: 10-21
• HazardClass: IRRITANT
• Hazardous Substances Data: 26690-80-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
TERT-BUTYL N-(2-HYDROXYETHYL)CARBAMATE is used as a protecting group for amines during the synthesis of complex organic compounds, such as phosphatidyl ethanolamines and ornithine. This application is crucial for the protection of amine groups, ensuring the successful synthesis of the target molecules.
Used in Chemical Synthesis:
In the field of chemical synthesis, TERT-BUTYL N-(2-HYDROXYETHYL)CARBAMATE serves as a difunctional reagent, enabling the formation of specific chemical bonds and facilitating the synthesis of desired products.
Used in Suzuki Reaction:
TERT-BUTYL N-(2-HYDROXYETHYL)CARBAMATE is also utilized in the Suzuki reaction, a widely used method for the formation of carbon-carbon bonds in organic chemistry. Its role in this reaction contributes to the efficient synthesis of various organic compounds with potential applications in pharmaceuticals, agrochemicals, and materials science.

Synthesis Reference(s)

Tetrahedron Letters, 28, p. 4185, 1987 DOI: 10.1016/S0040-4039(00)95574-6

InChI:InChI=1/C7H15NO3/c1-7(2,3)11-6(10)8-4-5-9/h9H,4-5H2,1-3H3,(H,8,10)

Upstream product

• 6627-89-0 tert-butyl phenyl carbonate 
• 141-43-5 ethanolamine 
• 24424-99-5 di-tert-butyl dicarbonate 
• 31954-27-5 N-(tert-butoxycarbonyl)glycine methyl ester 

Downstream Products

• 870194-68-6 [2-(2,4-bis-trifluoromethyl-phenoxy)-ethyl]-carbamic acid tert-butyl ester 
• 634925-24-9 tert-butyl (2-(benzyloxy)ethyl)carbamate 
• 265998-03-6 {2-[1-(3,4-dichloro-phenyl)-1-iodomethyl-3-trityloxy-propoxy]-ethyl}-carbamic acid tert-butyl ester 
• 247127-60-2 methyl 4-(2-tert-butoxycarbonylamino-ethoxy)-2-hydroxy-benzoate 
• 271245-28-4 {2-[1-(4-chloro-phenyl)-2-iodo-1-methyl-ethoxy]-ethyl}-carbamic acid tert-butyl ester 
• 51220-54-3 N-p-isopropyloxybenzoylglycine 
• 122234-46-2 2-iodo-1-<(tert-butyloxycarbonyl)amino>ethane 
• 54517-97-4 5-dimethylaminonaphthalene-1-sulfonic acid N-(propyl)amide 

Relevant articles and documents

Synthesis, biological evaluation, and molecular modeling studies of chiral chloroquine analogues as antimalarial agents

In a focused exploration, we designed, synthesized, and biologically evaluated chiral conjugated new chloroquine (CQ) analogues with substituted piperazines as antimalarial agents. In vitro as well as in vivo studies revealed that compound 7c showed potent activity (in vitro 50% inhibitory concentration, 56.98 nM for strain 3D7 and 97.76 nM for strain K1; selectivity index in vivo [up to at a dose of 12.5 mg/kg of body weight], 3,510) as a new lead antimalarial agent. Other compounds (compounds 6b, 6d, 7d, 7h, 8c, 8d, 9a, and 9c) also showed moderate activity against a CQ-sensitive strain (3D7) and superior activity against a CQ-resistant strain (K1) of Plasmodium falciparum. Furthermore, we carried out docking and three-dimensional quantitative structure-activity relationship (3D-QSAR) studies of all in-house data sets (168 molecules) of chiral CQ analogues to explain the structure-activity relationships (SAR). Our new findings specify the significance of the H-bond interaction with the side chain of heme for biological activity. In addition, the 3D-QSAR study against the 3D7 strain indicated the favorable and unfavorable sites of CQ analogues for incorporating steric, hydrophobic, and electropositive groups to improve the antimalarial activity.

Synthesis of chiral 3,4-disubstituted pyrroles from L-amino acids

A general methodology for the conversion of naturally occurring amino acids to 3,4-disubstituted pyrroles is described. A suitably protected amino acid (1) was first converted to the corresponding aldehyde (2). Homer-Emmons olefination afforded a facile entry to the corresponding α,β-unsaturated ester (3). The construction of the pyrrole ring system was accomplished in a single step, using an intramolecular cyclization reaction with tosylmethyl isocyanide (TOSMIC).

Palladium-catalyzed formation and stereoselective isomerization of 5- vinyloxazolines. Application to the formal synthesis of (S,S)-4-amino-3- hydroxy-5-phenylpentanoic acid

Vinyloxazolidinones have been found to undergo Pd(0)-catalyzed ionization followed by loss of carbon dioxide and subsequent cyclization to form vinyloxazolines. The reaction occurred under mild conditions, and enhancement of diastereomeric ratios with chiral substrates was obtained. 4- Benzyl-5-vinyloxazoline prepared by this method has been utilized in the stereoselective synthesis of (S,S)-4-amino-3-hydroxy-5-phenylpentanoic acid (AHPPA).

Total synthesis of perdeuterated phospholipids

A general method for the total synthesis of various perdeuterated phospholipids (DMPA, DMPG, DMPE, DMPC) is described.Starting from simple and easily obtainable deuterated precursors, perdeuterated phosphatidic acid (DMPA-d59) was synthesized.DMPA-d59 was coupled to various perdeuterated alcohols in the presence of alkylsulfonyl chlorides as condensing agents.The preparation of the perdeuterated alcohols is also presented.The major advantage of this method lies in the independent synthesis of DMPA and the alcohol moieties, allowing the transformation to the desired phospholipid class in the final reaction step.The reaction scheme presented here can also be used for the synthesis of selectively deuterated phospholipids.Keywords - perdeuterated phospholipids / phosphatidic acid-d59 / phosphatidylglycerol-d64 / phosphatidylcholine-d72 / phopshatidylethanolamine-d63 / total synthesis

Process for the preparation of acrylates

(Meth)acrylate esters containing an amine group blocked by a carbonate derivative having, e.g. t-butyl group, are made by reaction of a methyl or ethyl (meth)acrylate with a hydroxy carbamate derivative containing, e.g. a t-butyl group. The hydroxy carbamate derivative may be made by reacting an alkanolamine with an alkyl aryl carbonate in which the alkyl group is, e.g. t-butyl.