Arformoterol

Base Information

• Chemical Name: Arformoterol
• CAS No.: 73573-87-2
• Deprecated CAS: 208102-40-3,289657-27-8,299964-45-7,126587-85-7,49861-99-6,183814-29-1,289657-27-8,299964-45-7
• Molecular Formula: C19H24N2O4
• Molecular Weight: 344.411
• Hs Code.: 2924299090
• European Community (EC) Number: 615-991-0
• UNII: 5ZZ84GCW8B,F91H02EBWT
• DSSTox Substance ID: DTXSID40110071
• Nikkaji Number: J245.605B
• Wikipedia: Formoterol,Arformoterol
• Wikidata: Q4789167
• NCI Thesaurus Code: C47540,C61641,C65240,C65754
• RXCUI: 25255,236216,304962,668284
• Pharos Ligand ID: 8VK3JF52T893,8VKJ7WK1RNCS
• Metabolomics Workbench ID: 43475
• ChEMBL ID: CHEMBL1363
• Mol file: 73573-87-2.mol

Synonyms:3-formylamino-4-hydroxy-alpha-(N-1-methyl-2-p-methoxyphenethylaminomethyl)benzyl alcohol.hemifumarate;arformoterol;BD 40A;eformoterol;Foradil;formoterol;formoterol fumarate;formoterol fumarate, ((R*,R*)-(+-))-isomer;formoterol, ((R*,R*)-(+-))-isomer;Oxis

Chemical Property of Arformoterol

Chemical Property:

• Appearance/Colour: off-white solid
• Vapor Pressure: 2.12E-15mmHg at 25°C
• Refractive Index: 1.616
• Boiling Point: 603.2 °C at 760 mmHg
• PKA: 8.95±0.50(Predicted)
• Flash Point: 318.6 °C
• PSA: 90.82000
• Density: 1.233 g/cm³
• LogP: 3.32310
• Solubility.: DMSO: 20 mg/mL, soluble
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 8
• Exact Mass: 344.17360725
• Heavy Atom Count: 25
• Complexity: 388

Purity/Quality:

99.5% ^*data from raw suppliers

Formoterol-13C-d3 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CC1=CC=C(C=C1)OC)NCC(C2=CC(=C(C=C2)O)NC=O)O
• Isomeric SMILES: C[C@H](CC1=CC=C(C=C1)OC)NC[C@@H](C2=CC(=C(C=C2)O)NC=O)O
• Recent ClinicalTrials: A Pilot Study to Determine the Most Effective Dose of Arformoterol for Treating Acute Asthmatic Patients
• Recent EU Clinical Trials: Utility of inhaled extrafine triple therapy with glycopyrronium bromide, formoterol fumarate dihydrate and beclometasone dipropionate to improve expiratory flow limitation in severe COPD exacerbations. An double-blind randomized controlled trial.
• Recent NIPH Clinical Trials: A Randomized, Double-Blind, Double Dummy, Parallel Group, Multicenter Variable Length Study to Assess the Efficacy and Safety of PT010 Relative to PT009 and Symbicort in Adult and Adolescent Participants With Inadequately Controlled Asthma
• Uses: Labeled Formoterol, intended for use as an internal standard for the quantification of Formoterol by GC- or LC-mass spectrometry. Formoterol is a useful compound for treating respiratory obstructive diseases.

Technology Process of Arformoterol

There total 37 articles about Arformoterol 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:

(R,R)-N-(2-benzyloxy-5-{1-hydroxy-2-[[2-(4-methoxy-phenyl)-1-methyl-ethyl]-(1-phenyl-ethyl)-amino]-ethyl}-phenyl)-formamide (1316100-17-0) → (R,R)-formoterol (73573-87-2,67346-49-0)

Guidance literature:

With 5% Pd(II)/C(eggshell); hydrogen; In methanol; for 12h; under 2327.23 Torr;

DOI:10.1002/chir.20728

Reference yield:

(R)-2-bromo-1-(4-benzyloxy-3-nitrophenyl)ethanol (188690-82-6) → (R,R)-formoterol (73573-87-2,67346-49-0)

Guidance literature:

Multi-step reaction with 6 steps

1: K₂CO₃ / methanol / 2.5 h / 20 °C

2: dimethylsulfoxide / 87 h / 80 °C

3: neutral Al₂O₃ (activity III)

4: 67 percent / Fe turnings; 1M aq. HCl / methanol / 0.75 h / Heating

5: 69 percent / pyridine / 6.5 h / 60 °C

6: H₂ / 10 percentPd/C / ethanol / 20 °C

With pyridine; hydrogenchloride; aluminum oxide; hydrogen; iron; potassium carbonate; 10% palladium on active carbon; In methanol; ethanol; dimethyl sulfoxide; 1: Cyclization / 2: Addition / 3: Hydrolysis / 4: Reduction / 5: Formylation / 6: Hydrogenolysis;

DOI:10.1016/S0957-4166(00)00238-X

Reference yield:

4-benzyloxy-3-nitrophenacyl bromide (43229-01-2) → (R,R)-formoterol (73573-87-2,67346-49-0)

Guidance literature:

Multi-step reaction with 8 steps

1: 87 percent / BH₃*THF / tetrahydrofuran / -20 °C

2: lipase PS Celite-immobilized / various solvent(s) / 72 h / 37 °C

3: K₂CO₃ / methanol / 2.5 h / 20 °C

4: dimethylsulfoxide / 87 h / 80 °C

5: neutral Al₂O₃ (activity III)

6: 67 percent / Fe turnings; 1M aq. HCl / methanol / 0.75 h / Heating

7: 69 percent / pyridine / 6.5 h / 60 °C

8: H₂ / 10 percentPd/C / ethanol / 20 °C

With pyridine; hydrogenchloride; aluminum oxide; borane-THF; lipase PS Celite-immobilized; hydrogen; iron; potassium carbonate; 10% palladium on active carbon; In tetrahydrofuran; methanol; ethanol; dimethyl sulfoxide; 1: Reduction / 2: stereoselective / 3: Cyclization / 4: Addition / 5: Hydrolysis / 6: Reduction / 7: Formylation / 8: Hydrogenolysis;

DOI:10.1016/S0957-4166(00)00238-X

upstream raw materials:

N-[5-[(1R)-Hydroxy-2-[[(1R)-methyl-2-(4-methoxyphenyl)ethyl](phenylmethyl)amino]ethyl]-2-(phenylmethoxy)phenyl]-formamide

N-(2-Benzyloxy-5-{(R)-1-hydroxy-2-[(R)-2-(4-methoxy-phenyl)-1-methyl-ethylamino]-ethyl}-phenyl)-formamide

2-amino-1-(4-methyoxyphenyl)propane

1-methoxy-4-((E)-2-nitroprop-1-enyl)benzene

Downstream raw materials:

formoterol hemifumarate

N-[2-hydroxy-5-[(1R)-1-hydroxy-2-[[(1R)-(4-methoxyphenyl)-1-methylethyl]-amino]ethyl]phenyl]formamide

Refernces

• 1、 -. "PROCESSES FOR PREPARING SUBSTANTIALLY PURE ARFORMOTEROL AND ITS INTERMEDIATES". . . Retrieved 2012/01/13.
• 2、 Huang, Ling,Liu, Juntao,Shan, Wenjun,Liu, Bao,Shi, Anding,Li, Xingshu. "The asymmetric synthesis of (R,R)-formoterol via transfer hydrogenation with polyethylene glycol bound Rh catalyst in PEG2000 and water". experimental part. p. 206 - 211. Retrieved 2010/11/18.