518047-98-8

Basic information

• Product Name: BENZYL [2-AMINO-2-(HYDROXYIMINO)-1,1-DIMETHYLETHYL]CARBAMATE
• Synonyms: BENZYL [2-AMINO-2-(HYDROXYIMINO)-1,1-DIMETHYLETHYL]CARBAMATE;Raltegravir II;Benzyl N-[1-(N'-hydroxycarbamimidoyl)-1-methylethyl]carbamate;RTG3;N-[2-(HydroxyaMino)-2-iMino-1,1-diMethylethyl]-carbaMic Acid Benzyl Ester;N-[2-(HydroxyaMino)-2-iMino-1,1-diMethylethyl]-carbaMic Acid PhenylMethyl Ester;CarbaMicacid, N-[2-(hydroxyaMino)-2-iMino-1,1-diMethylethyl]-, phenylMethyl ester;(Z)-benzyl (1-aMino-1-(hydroxyiMino)-2-Methylpropan-2-yl)carbaMate
• CAS NO: 518047-98-8
• Molecular Formula: C₁₂H₁₇N₃O₃
• Molecular Weight: 251.28
• Product Categories: Amines;Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 518047-98-8.mol
• Article Data: 12

Chemical Properties

• Melting Point: 160.0-160.5 °C
• Appearance: /
• Density: 1.2 g/cm³
• Refractive Index: 1.552
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility: Chloroform (Slightly, Heated), DMSO (Slightly), Ethyl Acetate (Slightly), Methan
• PKA: 6.97±0.69(Predicted)
• CAS DataBase Reference: BENZYL [2-AMINO-2-(HYDROXYIMINO)-1,1-DIMETHYLETHYL]CARBAMATE(CAS DataBase Reference)
• NIST Chemistry Reference: BENZYL [2-AMINO-2-(HYDROXYIMINO)-1,1-DIMETHYLETHYL]CARBAMATE(518047-98-8)
• EPA Substance Registry System: BENZYL [2-AMINO-2-(HYDROXYIMINO)-1,1-DIMETHYLETHYL]CARBAMATE(518047-98-8)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 518047-98-8(Hazardous Substances Data)

Usage

Chemical Properties

Colourless Solid

Uses

An intermediate in the preparation of HIV-integrase inhibitors

InChI:InChI=1/C12H17N3O3/c1-12(2,10(13)15-17)14-11(16)18-8-9-6-4-3-5-7-9/h3-7,17H,8H2,1-2H3,(H2,13,15)(H,14,16)

Upstream product

• 15030-72-5 Z-Aib-OH 
• 81587-18-0 benzyl N-(2-amino-1,1-dimethyl-2-oxo-ethyl)carbamate 
• 100134-82-5 (cyano-dimethyl-methyl)carbamic acid benzyl ester 
• 501-53-1 benzyl chloroformate 

Downstream Products

• 519028-33-2 {1-[4-(4-fluoro-benzylcarbamoyl)-5,6-dihydroxy-pyrimidin-2-yl]-1-methyl-ethyl}-carbamic acid benzyl ester 
• 518048-02-7 {1-[4-(4-fluoro-benzylcarbamoyl)-5-hydroxy-1-methyl-6-oxo-1,6-dihydro-pyrimidin-2-yl]-1-methyl-ethyl}carbamic acid benzyl ester 
• 519028-40-1 C₂₄H₂₅FN₄O₅ 
• 888504-27-6 2-(1-benzyloxycarbonylamino-1-methyl-ethyl)-5-hydroxy-1-methyl-6-oxo-1,6-dihydro-pyrimidine-4-carboxylic acid methyl ester 
• 1159977-42-0 C₁₈H₂₁N₃O₆ 
• 1172131-65-5 C₂₉H₃₃FN₄O₆ 
• 1028026-63-2 C₁₈H₂₃N₃O₇ 
• 1028026-73-4 C₁₈H₂₃N₃O₇ 
• 857664-99-4 methyl 5-(benzoyloxy)-2-(2-(benzyloxycarbonylamino)propan-2-yl)-6-methoxypyrimidine-4-carboxylate 
• 518048-01-6 methyl 5-(benzoyloxy)-2-(1-{[(benzyloxy)carbonyl]amino}-1-methylethyl)-1-methyl-6-oxo-1,6-dihydropyrimidine-4-carboxylate 
• 518048-00-5 methyl 5-(benzoyloxy)-2-(2-(benzyloxycarbonylamino)propan-2-yl)-6-oxo-1,6-dihydropyrimidine-4-carboxylate 
• 519032-08-7 methyl 2-(1-{[(benzyloxy) carbonyl] amino}-1-methylethyl)-5,6-dihydroxypyrimidine-4-carboxylate 
• 1415000-08-6 C₂₄H₂₃F₃N₄O₅ 
• 1415000-07-5 C₂₄H₂₆N₄O₅ 

Relevant articles and documents

A Scalable Synthesis of 2-(1,2,4-Oxadiazol-3-yl)propan-2-amine Hydrobromide Using a Process Safety-Driven Protecting Group Strategy

A safe and scalable synthesis of 2-(1,2,4-oxadiazol-3-yl)propan-2-amine hydrobromide is described. A process safety-driven synthetic strategy was employed for the selection of thermally stable compounds en route to the target 1,2,4-oxadiazole. Application

Structural modifications of 5,6-dihydroxypyrimidines with anti-HIV activity

A series of 5,6-dihydroxypyrimidine analogs were synthesized and evaluated for their anti-HIV activity in vitro. Among all of the analogs, several compounds exhibited significant anti-HIV activity, especially 1b and 1e, which showed the most potent anti-HIV activity with EC50 values of 0.14 and 0.15 μM, and TI (therapeutic index) values of >300 and >900, respectively. Further docking studies revealed that the representative compounds 1e and 3a could meet the HIV-1 integrase inhibition minimal requirements of a chelating domain (two metal ions) and an aromatic domain (π-π stacking interactions).

Development of a second-generation, highly efficient manufacturing route for the HIV integrase inhibitor raltegravir potassium

A manufacturing route for the synthesis of raltegravir potassium 1 was developed via a thermal rearrangement of amidoxime DMAD adducts 6 to construct the key, highly functionalized hydroxypyrimidinone core 7. Utilizing this route 1 was prepared in nine linear chemical steps with 22% overall yield. A second-generation synthesis was subsequently developed that solved the key chemical, productivity, and environmental impact issues of the initial synthesis. Highlights of the new synthesis include a highly selective methylation, 3-4-fold higher productivity, and a 65% reduction of combined organic and aqueous waste produced. The efficient second-generation manufacturing route provides raltegravir potassium 1 in 35% overall yield.