benzyl N-(1-amino-1-hydroxyimino-2-methylpropan-2-yl)carbamate

Base Information

• Chemical Name: benzyl N-(1-amino-1-hydroxyimino-2-methylpropan-2-yl)carbamate
• CAS No.: 518047-98-8
• Molecular Formula: C12H17N3O3
• Molecular Weight: 251.285
• Hs Code.: 2928000090
• European Community (EC) Number: 610-731-2
• Mol file: 518047-98-8.mol

Synonyms:518047-98-8;Benzyl [2-amino-2-(hydroxyimino)-1,1-dimethylethyl]carbamate;Benzyl (1-amino-1-(hydroxyimino)-2-methylpropan-2-yl)carbamate;1-amino-2-(1-methyl-1-phenoxycarbonylamino-ethyl)-oxime;benzyl N-[(1Z)-1-amino-1-hydroxyimino-2-methylpropan-2-yl]carbamate;AKOS030242360;FT-0662680

Chemical Property of benzyl N-(1-amino-1-hydroxyimino-2-methylpropan-2-yl)carbamate

Chemical Property:

• Melting Point: 160.0-160.5 °C
• Refractive Index: 1.552
• PKA: 6.97±0.69(Predicted)
• PSA: 96.94000
• Density: 1.2 g/cm³
• LogP: 2.52900
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility.: Chloroform (Slightly, Heated), DMSO (Slightly), Ethyl Acetate (Slightly), Methan
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 251.12699141
• Heavy Atom Count: 18
• Complexity: 310

Purity/Quality:

98% ^*data from raw suppliers

Benzyl[2-Amino-2-(hydroxyimino)-1,1-dimethylethyl]carbamate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C(=NO)N)NC(=O)OCC1=CC=CC=C1
• Uses: An intermediate in the preparation of HIV-integrase inhibitors

Technology Process of benzyl N-(1-amino-1-hydroxyimino-2-methylpropan-2-yl)carbamate

There total 5 articles about benzyl N-(1-amino-1-hydroxyimino-2-methylpropan-2-yl)carbamate 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: 91.0%

(cyano-dimethyl-methyl)carbamic acid benzyl ester (100134-82-5) → [1-(N'-hydroxycarbamimidoyl)-1-methyl-ethyl]carbamic acid benzyl ester (518047-98-8)

Guidance literature:

With hydroxylamine; In water; isopropyl alcohol; at 58 - 60 ℃; for 5.42h; Large scale reaction;

DOI:10.1021/op100257r

Reference yield: 88.0%

(cyano-dimethyl-methyl)carbamic acid benzyl ester (100134-82-5) → benzyl [2-amino-2-(hydroxyimino)-1,1-dimethylethyl]carbamate (518047-98-8)

Guidance literature:

With hydroxylamine; In water; isopropyl alcohol; at 60 ℃; for 3.33333h;

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) → benzyl [2-amino-2-(hydroxyimino)-1,1-dimethylethyl]carbamate (518047-98-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 99 percent / Na₂CO₃ / 20 °C

2: NH₂OH / methanol / 60 °C

With hydroxylamine; sodium carbonate; In methanol;

DOI:10.1021/jm070027u

upstream raw materials:

(cyano-dimethyl-methyl)carbamic acid benzyl ester

benzyl chloroformate

Z-Aib-OH

benzyl N-(2-amino-1,1-dimethyl-2-oxo-ethyl)carbamate

Downstream raw materials:

methyl 5-(benzoyloxy)-2-(2-(benzyloxycarbonylamino)propan-2-yl)-6-methoxypyrimidine-4-carboxylate

methyl 5-(benzoyloxy)-2-(1-{[(benzyloxy)carbonyl]amino}-1-methylethyl)-1-methyl-6-oxo-1,6-dihydropyrimidine-4-carboxylate

methyl 5-(benzoyloxy)-2-(2-(benzyloxycarbonylamino)propan-2-yl)-6-oxo-1,6-dihydropyrimidine-4-carboxylate

methyl 2-(1-{[(benzyloxy) carbonyl] amino}-1-methylethyl)-5,6-dihydroxypyrimidine-4-carboxylate

Refernces

• 1、 Wang, Ziwen,Wang, Mingxiao,Yao, Xue,Li, Yue,Qiao, Wentao,Geng, Yunqi,Liu, Yuxiu,Wang, Qingmin. "Hydroxyl may not be indispensable for raltegravir: Design, synthesis and SAR Studies of raltegravir derivatives as HIV-1 inhibitors". experimental part. p. 361 - 369. Retrieved 2012/06/30.
• 2、 Patil, Gulabrao D.,Kshirsagar, Siddheshwar W.,Shinde, Shivnath B.,Patil, Pankaj S.,Deshpande, Mangesh S.,Chaudhari, Ashok T.,Sonawane, Swapnil P.,Maikap, Golak C.,Gurjar, Mukund K.. "Identification, synthesis, and strategy for minimization of potential impurities observed in raltegravir potassium drug substance". . p. 1422 - 1429. Retrieved 2012/10/29.