(r)-1-(Benzyloxy)-3-butylazetidin-2-one

Base Information

• Chemical Name: (r)-1-(Benzyloxy)-3-butylazetidin-2-one
• CAS No.: 676127-84-7
• Molecular Formula: C14H19NO2
• Molecular Weight: 233.31
• DSSTox Substance ID: DTXSID40581287
• Mol file: 676127-84-7.mol

Synonyms:(r)-1-(benzyloxy)-3-butylazetidin-2-one;676127-84-7;(3R)-3-butyl-1-phenylmethoxyazetidin-2-one;2-Azetidinone, 3-butyl-1-(phenylmethoxy)-, (3R)-;(3R)-1-(Benzyloxy)-3-butylazetidin-2-one;SCHEMBL4317709;DTXSID40581287;NJLUCYJPLCEOLR-CYBMUJFWSA-N;(3R)-3-Butyl-1-[(phenylmethyl)oxy]-2-azetidinone

Chemical Property of (r)-1-(Benzyloxy)-3-butylazetidin-2-one

Chemical Property:

• XLogP3: 3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 6
• Exact Mass: 233.141578849
• Heavy Atom Count: 17
• Complexity: 249

Purity/Quality:

99%,98%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCC1CN(C1=O)OCC2=CC=CC=C2
• Isomeric SMILES: CCCC[C@@H]1CN(C1=O)OCC2=CC=CC=C2

Technology Process of (r)-1-(Benzyloxy)-3-butylazetidin-2-one

There total 12 articles about (r)-1-(Benzyloxy)-3-butylazetidin-2-one 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: 50.0%

2-[[(phenylmethoxy)amino]methyl]-(2R)-hexanoic acid methyl ester → (3R)-3-butyl-1-[(phenylmethyl)oxy]-2-azetidinone (676127-84-7)

Guidance literature:

2-[[(phenylmethoxy)amino]methyl]-(2R)-hexanoic acid methyl ester; With methylmagnesium chloride; In tetrahydrofuran; at 0 - 3 ℃; for 1h;

pH=7; Phosphate buffer;

Reference yield:

(2R)-2-(hydroxymethyl)-N-[(phenylmethyl)oxy]hexanamide (676127-81-4) → (3R)-3-butyl-1-[(phenylmethyl)oxy]-2-azetidinone (676127-84-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 98 percent / pyridine

2: K₂CO₃; tetrabutylammonium bromide / tetrahydrofuran / 6 h / 40 °C

With pyridine; tetrabutylammomium bromide; potassium carbonate; In tetrahydrofuran;

DOI:10.1055/s-2006-951499

Reference yield:

(R)-2-butyl-3-hydroxypropionic acid → (3R)-3-butyl-1-[(phenylmethyl)oxy]-2-azetidinone (676127-84-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; sodium hydroxide / water

2: pyridine

3: tetrabutylammomium bromide; potassium carbonate / tetrahydrofuran

With pyridine; tetrabutylammomium bromide; potassium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; sodium hydroxide; In tetrahydrofuran; water;

DOI:10.1016/j.bmcl.2010.12.097

upstream raw materials:

(2R)-2-(hydroxymethyl)-N-[(phenylmethyl)oxy]hexanamide

O-benzylhydoxylamine hydrochloride

2-butylpropane-1,3-diol

(±)-2-butyl-3-hydroxypropionic acid

Downstream raw materials:

C₂₄H₃₁FN₄O₃

(S)-1-{(R)-2-[(Formyl-hydroxy-amino)-methyl]-hexanoyl}-pyrrolidine-2-carboxylic acid (5-fluoro-1-oxy-pyridin-2-yl)-amide

(2S)-N-(5-fluoro-2-pyridinyl)-1-[(2R)-2-[formyl(phenylmethoxy)amino]methyl]-1-oxohexyl-2-pyrrolidinecarboxamide

(2S)-N-(5-fluoro-1-oxido-2-pyridinyl)-1-[(2R)-2-[[formyl(phenylmethoxy)amino]methyl]-1-oxohexyl]-2-pyrrolidinecarboxamide