(1R,4S)-tert-Butyl 3-oxo-2-azabicyclo[2.2.1]hept-5-ene-2-carboxylate

Base Information

• Chemical Name: (1R,4S)-tert-Butyl 3-oxo-2-azabicyclo[2.2.1]hept-5-ene-2-carboxylate
• CAS No.: 151792-53-9
• Molecular Formula: C11H15NO3
• Molecular Weight: 209.24200
• DSSTox Substance ID: DTXSID00474101
• Nikkaji Number: J1.114.743G
• Wikidata: Q82303892
• Mol file: 151792-53-9.mol

Synonyms:151792-53-9;(1R,4S)-tert-Butyl 3-oxo-2-azabicyclo[2.2.1]hept-5-ene-2-carboxylate;tert-butyl (1R,4S)-3-oxo-2-azabicyclo[2.2.1]hept-5-ene-2-carboxylate;(6R,7S)-2-BOC-2-AZA-BICYCLO[2.2.1]HEPT-5-EN-3-ONE;RACEMIC-(1R,4S)-TERT-BUTYL 3-OXO-2-AZABICYCLO[2.2.1]HEPT-5-ENE-2-CARBOXYLATE;MFCD11504994;NQIZWJGHIYDHRL-SFYZADRCSA-N;SCHEMBL782700;DTXSID00474101;CS-M2481;AKOS016003195;2-Azabicyclo[2.2.1]hept-5-ene-2-carboxylic acid, 3-oxo-, 1,1-dimethylethyl ester, (1R,4S)-;CS-14644;E87269;W14137;(1R, 4S)-N-tert-butoxycarbonyl-2-azabicyclo[2.2.1]hept-5-en-3-one;(1R,4S) -N-tert-butoxycarbonyl-2-azabicyclo[2.2.1]hept-5-en-3-one;(1R,4S)-N-tert-butoxycarbonyl-2-azabicyclo[2.2.1]hept-5-en-3-one;(1R,4S)-t-Butyl 3-oxo-2-azabicyclo[2.2.1]hept-5-ene-2-carboxylate;(1R,4S)-tert-butyl 3-oxo-2-azabicyclo[2.2.1]hept-5-ene-2- carboxylate;(1R,4S)-tert-Butyl3-oxo-2-azabicyclo[2.2.1]hept-5-ene-2-carboxylate

Chemical Property of (1R,4S)-tert-Butyl 3-oxo-2-azabicyclo[2.2.1]hept-5-ene-2-carboxylate

Chemical Property:

• Melting Point: 85.0-86.5 °C
• Boiling Point: 339.8±31.0 °C(Predicted)
• PKA: -2.32±0.20(Predicted)
• PSA: 46.61000
• Density: 1?+-.0.06 g/cm3(Predicted)
• LogP: 1.64630
• Storage Temp.: 2-8°C
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 209.10519334
• Heavy Atom Count: 15
• Complexity: 340

Purity/Quality:

99% ^*data from raw suppliers

(1R,?4S)?-3-?Oxo-2-?azabicyclo[2.2.1]?hept-?5-?ene-?2-?carboxylicacid1,?1-?DimethylethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1C2CC(C1=O)C=C2
• Isomeric SMILES: CC(C)(C)OC(=O)N1[C@@H]2C[C@H](C1=O)C=C2
• Uses: (1R,?4S)?-3-?Oxo-2-?azabicyclo[2.2.1]?hept-?5-?ene-?2-?carboxylic acid 1,?1-?Dimethylethyl Ester is an intermediate in synthesizing ent-Abacavir (Abacavir EP Impurity A) (A105015), an enatiomer of Abacavir (A105000). Abacavir is a carbocyclic 2''-deoxyguanosine nucleoside reverse transcriptase inhibitor and an anti-HIV drug used to treat HIV infection (1). Intracellular enzymes convert Abacavir to its active form, carbovir-triphosphate (CBV-TP), which then selectively inhibits HIV reverse transcriptase by incorporating into viral DNA (2). Abacavir is metabolized in the liver by uridine diphosphate glucuronyltransferase and alcohol dehydrogenase resulting in inactive glucuronide and carboxylate metabolites, respectively.

Technology Process of (1R,4S)-tert-Butyl 3-oxo-2-azabicyclo[2.2.1]hept-5-ene-2-carboxylate

There total 27 articles about (1R,4S)-tert-Butyl 3-oxo-2-azabicyclo[2.2.1]hept-5-ene-2-carboxylate 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: 100.0%

di-tert-butyl dicarbonate (24424-99-5) + (-)-2-azabicyclo[2.2.1]hept-5-en-3-one (79200-56-9) → tert-butyl (1R,4S)-(-)-3-oxo-2-azabicyclo[2.2.1]hept-5-ene-2-carboxylate (151792-53-9)

Guidance literature:

With dmap; triethylamine; In tetrahydrofuran;

Reference yield: 84.0%

(±)-tert-butyl 3-oxo-2-azabicyclo[2.2.1]hept-5-ene-2-carboxylate → tert-butyl (1R,4S)-(-)-3-oxo-2-azabicyclo[2.2.1]hept-5-ene-2-carboxylate (151792-53-9)

Guidance literature:

Savinase; In tetrahydrofuran; phosphate buffer; at 30 ℃; for 48h; pH=8; Enzymatic reaction;

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) + (+)-2-Azabicyclo<2.2.1>heptan-3-one (134003-03-5) → tert-butyl (1R,4S)-(-)-3-oxo-2-azabicyclo[2.2.1]hept-5-ene-2-carboxylate (151792-53-9)

Guidance literature:

With dmap; In acetonitrile; at 25 ℃; for 1h;

DOI:10.1016/j.ejmech.2021.113272

upstream raw materials:

di-tert-butyl dicarbonate

(-)-2-azabicyclo[2.2.1]hept-5-en-3-one

3-oxo-2-aza-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid tert-butyl ester

2-azabicyclo[2.2.1.]hept-5-en-3-one

Downstream raw materials:

(1S-cis)-4-[[(1,1-dimethylethoxy)carbonyl]amino]-2-cyclopentene-1-carboxylic acid

methyl (1R,4R)-4-(tert-butoxycarbonylamino)cyclopent-2-ene-1-carboxylate

(1S,4R)-(-)-methyl-[[(1,1-dimethylethoxy)carbonyl]amino]cyclopent-2-ene-1-carboxylate

C₁₁H₁₇NO₄