(6-Tert-butoxycarbonylaminopyridin-3-yl) acetic acid

Base Information

• Chemical Name: (6-Tert-butoxycarbonylaminopyridin-3-yl) acetic acid
• CAS No.: 1256337-02-6
• Molecular Formula: C₁₂H₁₆N₂O₄
• Molecular Weight: 252.27
• European Community (EC) Number: 842-625-9
• DSSTox Substance ID: DTXSID901182626
• Mol file: 1256337-02-6.mol

Synonyms:1256337-02-6;(6-tert-butoxycarbonylaminopyridin-3-yl) acetic acid;2-[6-[(2-methylpropan-2-yl)oxycarbonylamino]pyridin-3-yl]acetic acid;2-(6-((tert-Butoxycarbonyl)amino)pyridin-3-yl)acetic acid;3-Pyridineacetic acid, 6-[[(1,1-dimethylethoxy)carbonyl]amino]-;starbld0017207;(6-TERT-BUTOXYCARBONYLAMINO-PYRIDIN-3-YL)-ACETIC ACID;SCHEMBL949620;OXQVDWZWFHQQLU-UHFFFAOYSA-N;DTXSID901182626;EN300-1603758;A935208;Z1505702860;2-(6-{[(tert-butoxy)carbonyl]amino}pyridin-3-yl)acetic acid;6-[[(1,1-Dimethylethoxy)carbonyl]amino]-3-pyridineacetic acid

Chemical Property of (6-Tert-butoxycarbonylaminopyridin-3-yl) acetic acid

Chemical Property:

• XLogP3: 1.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 252.11100700
• Heavy Atom Count: 18
• Complexity: 312

Purity/Quality:

98% ^*data from raw suppliers

(6-tert-Butoxycarbonylamino-pyridin-3-yl)-aceticacid 95 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC1=NC=C(C=C1)CC(=O)O

Technology Process of (6-Tert-butoxycarbonylaminopyridin-3-yl) acetic acid

There total 4 articles about (6-Tert-butoxycarbonylaminopyridin-3-yl) acetic acid 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: 49.0%

ethyl (6-tert-butoxycarbonylaminopyridin-3-yl)acetate (1256337-01-5) → (6-tert-butoxycarbonylaminopyridin-3-yl) acetic acid (1256337-02-6)

Guidance literature:

With water; sodium hydroxide; In methanol; for 1.5h; Reflux;

DOI:10.1002/anie.201207925

Reference yield:

(6-chloro-pyridin-3-yl)-acetonitrile (39891-09-3) → (6-tert-butoxycarbonylaminopyridin-3-yl) acetic acid (1256337-02-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sulfuric acid / water / 5 h / Reflux

1.2: 20 °C

2.1: caesium carbonate / tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / tetrahydrofuran / 20 h / Heating; Inert atmosphere; Reflux

3.1: methanol; water; sodium hydroxide / 1.5 h / Reflux

3.2: pH 4 - 5

With methanol; water; caesium carbonate; sodium hydroxide; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; sulfuric acid; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In tetrahydrofuran; water;

Reference yield:

2-chloro-5-(chloromethyl)pyridine (70258-18-3) → (6-tert-butoxycarbonylaminopyridin-3-yl) acetic acid (1256337-02-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: ethanol; water / 20 h / 20 °C / Reflux

2.1: sulfuric acid / water / 5 h / Reflux

2.2: 20 °C

3.1: caesium carbonate / tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / tetrahydrofuran / 20 h / Heating; Inert atmosphere; Reflux

4.1: methanol; water; sodium hydroxide / 1.5 h / Reflux

4.2: pH 4 - 5

With methanol; water; caesium carbonate; sodium hydroxide; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; sulfuric acid; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In tetrahydrofuran; ethanol; water;

upstream raw materials:

ethyl (6-tert-butoxycarbonylaminopyridin-3-yl)acetate

(6-chloro-pyridin-3-yl)-acetonitrile

2-chloro-5-(chloromethyl)pyridine

ethyl (6-chloro-pyridin-3-yl)acetate