85006-25-3

Basic information

• Product Name: TERT-BUTYL N-(TERT-BUTOXYCARBONYLOXY)CARBAMATE
• Synonyms: TERT-BUTYL N-(TERT-BUTOXYCARBONYLOXY)CARBAMATE;N,O-DI-BOC-HYDROXYLAMINE;N,O-BIS-BOC-HYDROXYLAMINE;N,O-BIS(TERT-BUTOXYCARBONYL)HYDROXYLAMINE;N,O-Bis(tert-butoxycarbonyl)hydroxylamine;oxycarbamate;tert-Butyl (tert-butoxycarbonyl);DBNOH
• CAS NO: 85006-25-3
• Molecular Formula: C₁₀H₁₉NO₅
• Molecular Weight: 233.26
• EINECS: 285-055-0
• Product Categories: Building Blocks;Chemical Synthesis;Nitrogen Compounds;Organic Building Blocks;Protected Amines
• Mol File: 85006-25-3.mol

Chemical Properties

• Melting Point: 67-70 °C(lit.)
• Appearance: White crystalline powder
• Density: 1.080
• Refractive Index: 1.442
• Storage Temp.: −20°C
• BRN: 1794022
• CAS DataBase Reference: TERT-BUTYL N-(TERT-BUTOXYCARBONYLOXY)CARBAMATE(CAS DataBase Reference)
• NIST Chemistry Reference: TERT-BUTYL N-(TERT-BUTOXYCARBONYLOXY)CARBAMATE(85006-25-3)
• EPA Substance Registry System: TERT-BUTYL N-(TERT-BUTOXYCARBONYLOXY)CARBAMATE(85006-25-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• F: 10-21
• Hazardous Substances Data: 85006-25-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
TERT-BUTYL N-(TERT-BUTOXYCARBONYLOXY)CARBAMATE is used as a synthetic intermediate for the development of pharmaceutical compounds. Its ability to protect hydroxyl and amine groups makes it a valuable component in the synthesis of complex organic molecules, including drug candidates.
Used in Synthesis of 5-Lipoxygenase Inhibitor LY280810:
In the pharmaceutical industry, TERT-BUTYL N-(TERT-BUTOXYCARBONYLOXY)CARBAMATE is used as a key intermediate in the synthesis of LY280810, a potent 5-lipoxygenase inhibitor. TERT-BUTYL N-(TERT-BUTOXYCARBONYLOXY)CARBAMATE has potential applications in the treatment of inflammatory diseases by inhibiting the production of leukotrienes, which are involved in the inflammatory process.
Used in Synthesis of Hydroxylamines:
TERT-BUTYL N-(TERT-BUTOXYCARBONYLOXY)CARBAMATE is used as a starting material for the synthesis of hydroxylamines, which are important intermediates in the production of various organic compounds, including pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Synthesis of Hydroxamic Acids:
In the field of organic chemistry, TERT-BUTYL N-(TERT-BUTOXYCARBONYLOXY)CARBAMATE is used as a precursor in the synthesis of hydroxamic acids. These compounds have a wide range of applications, including as chelating agents, inhibitors of metalloenzymes, and in the development of pharmaceuticals targeting various biological targets.

Synthesis Reference(s)

Journal of the American Chemical Society, 81, p. 955, 1959 DOI: 10.1021/ja01513a049Tetrahedron Letters, 34, p. 7043, 1993 DOI: 10.1016/S0040-4039(00)61592-7

InChI:InChI=1/C10H19NO5/c1-9(2,3)14-7(12)11-16-8(13)15-10(4,5)6/h1-6H3,(H,11,12)

Upstream product

• 1070-19-5 N-(tert-butyloxycarbonyl) azide 
• 36016-38-3 tert-Butyl N-hydroxycarbamate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 870-46-2 t-butoxycarbonylhydrazine 
• 5470-11-1 hydroxylamine hydrochloride 

Downstream Products

• 159879-43-3 C₁₉H₂₇NO₅ 
• 159879-41-1 tert-butylbenzyl((tert-butoxycarbonyl)oxy)carbamate 
• 159879-42-2 C₁₇H₂₄N₂O₇ 
• 66508-11-0 3-(N-hydroxyamino)-propylphosphonic acid 
• 178323-49-4 C₂₅H₃₁NO₅ 
• 178323-59-6 N-tert-butoxycarbonyloxy-N-[3-(4-methoxyphenyl)-3-phenylallyl]carbamic acid tert-butyl ester 
• 178323-51-8 C₂₆H₃₃NO₆ 
• 178323-50-7 C₂₆H₃₃NO₆ 
• 138561-27-0 C₂₉H₃₅ClN₂O₇ 
• 4114-28-7 diethyl hydrazodicarboxylate 
• 791-28-6 Triphenylphosphine oxide 
• 180294-88-6 dimethyl {3-[(tert-butoxycarbonyl)(tert-butoxycarbonyloxy)amino]-1-cyclohexen-1-yl}phosphonate 

Relevant articles and documents

A Facile Synthesis of N,O-bis(tert-butoxycarbonyl)-Hydroxylamine

N,O-bis(tert-butoxycarbonyl)hydroxylamine was synthesized in 85percent yield from hydroxylamine hydrochloride and di-tert-butyl dicarbonate in the presence of triethylamine.The chemistry is facile, utilizes readily available reagents and represents an improvement in safety over the previously published method.

Total Synthesis of Isodihydrokoumine, (19 Z)-Taberpsychine, and (4 R)-Isodihydroukoumine N4-Oxide

We report the total synthesis of the natural products isodihydrokoumine and (19Z)-taberpsychine in 11 steps each and (4R)-isodihydrokoumine N4-oxide in 12 steps from commercially available starting materials. The key reactions include an intramolecular [3 + 2] nitrone cycloaddition and Lewis acid mediated cyclizations of a common intermediate to provide the core structures of either taberpsychine or isodihydrokoumine.

Novel Polyamine-Naphthalene Diimide Conjugates Targeting Histone Deacetylases and DNA for Cancer Phenotype Reprogramming

A series of hybrid compounds was designed to target histone deacetylases and ds-/G-quadruplex DNAs by merging structural features deriving from Scriptaid and compound 1. Compound 6 binds different DNA arrangements, inhibits HDACs both in vitro and in cells, and is able to induce a reduction of cell proliferation. Moreover, compound 6 displays cell phenotype-reprogramming properties since it prevents the epithelial to mesenchymal transition in cancer cells, inducing a less aggressive and migratory phenotype, which is one of the goals of present innovative strategies in cancer therapies.

AMINOTHIAZINE COMPOUNDS

The present invention provides a compound of Formula (I); or a pharmaceutically acceptable salt thereof.

BACE INHIBITORS

The present invention provides compounds of Formula I useful as BACE inhibitors in the treatment of e.g. Alzheimer's disease : wherein A is selected from the group consisting of; of; R1 is H or F; R2 is H, -OCH3, C1-C3 alkyl,; R3 is H, -CH3, or -OCH3; and R4 is H or F; or a pharmaceutically acceptable salt thereof.

One-pot synthesis of fused pyrroles through a key gold-catalysis-triggered cascade

A two-step, one-pot synthesis of fused pyrroles is realized by firstly condensing an N-alkynylhydroxammonium salt with a readily enolizable ketone under mild basic conditions and then subjecting the reaction mixture to a gold catalyst, which triggers a cascade reaction involving a facile initial [3.3]-sigmatropic rearrangement of the gold-catalysis product, that is, an N,O-dialkenylhydroxamine. The reaction provides a facile access to polycyclic pyrroles in moderate to good yields. A two-step, one-pot synthesis of fused pyrroles is realized by firstly condensing an N-alkynylhydroxammonium salt with a readily enolizable ketone under mild basic conditions and then subjecting the reaction mixture to a gold catalyst, which triggers a cascade reaction involving a facile initial [3.3]-sigmatropic rearrangement of the gold-catalysis product, that is, an N,O-dialkenylhydroxamine. The reaction provides a facile access to polycyclic pyrroles in moderate to good yields (see scheme). Copyright

MELDRUM 'S ACID, BARBITURIC ACID AND PYRAZOLONE DERIVATIVES SUBSTITUTED WITH HYDROXYLAMINE AS HNO DONORS

The disclosed subject matter provides certain N-substituted hydroxylamine derivative compounds, pharmaceutical compositions and kits comprising such compounds, and methods of using such compounds or pharmaceutical compositions. In particular, the disclosed subject matter provides methods of using such compounds or pharmaceutical compositions for treating, preventing, or delaying the onset and/or development of a disease or condition. In some embodiments, the disease or condition is selected from cardiovascular diseases, ischemia, reperfusion injury, cancerous disease, pulmonary hypertension and conditions responsive to nitroxyl therapy.

Development of N-substituted hydroxylamines as efficient nitroxyl (HNO) donors

Due to its inherent reactivity, nitroxyl (HNO), must be generated in situ through the use of donor compounds, but very few physiologically useful HNO donors exist. Novel N-substituted hydroxylamines with carbon-based leaving groups have been synthesized, and their structures confirmed by X-ray crystallography. These compounds generate HNO under nonenzymatic, physiological conditions, with the rate and amount of HNO released being dependent mainly on the nature of the leaving group. A barbituric acid and a pyrazolone derivative have been developed as efficient HNO donors with half-lives at pH 7.4, 37 °C of 0.7 and 9.5 min, respectively.

IMPROVED AMINOHYDROXYLATION OF ALKENES

The invention relates to a process for the aminohydroxylation of alkenes using N-oxycarbamate reagents, e.g. N-acyloxycarbamate, N-alkyloxycarbonyloxycarbamate and N-aralkoxycarbonyloxycarbamate reagents. The invention particularly relates to an intermolecular aminohydroxylation reaction that can be carried out in the absence of added base. The invention also relates to novel N-oxycarbamate reagents that are stable crystalline materials. The process of the invention is useful in the synthesis of compounds having a vicinal amino alcohol moiety, such as biologically active compounds.

A regio- and diastereoselective intramolecular nitrone cycloaddition for practical 3- and 2,3-disubstituted piperidine synthesis from γ-butyrolactone

(Chemical Equation Presented) A fast and efficient route for diversity-oriented synthesis of 3- and 2,3-disubstituted piperidines, featuring an intramolecular nitrone cycloaddition with high regio- and diastereoselectivity, was achieved in six steps and 36-66% overall yield from commercially available γ-butyrolactone or 1,4-butanediol. A new N-alkenyl nitrone enoate was used in this intramolecular nitrone cycloaddition, and the regioselectivity, diastereoselectivity, and reversibility of this cycloaddition were investigated.