alpha-Cyclopentylmandelic acid

Base Information

• Chemical Name: alpha-Cyclopentylmandelic acid
• CAS No.: 427-49-6
• Molecular Formula: C13H16O3
• Molecular Weight: 220.268
• Hs Code.: 29163990
• European Community (EC) Number: 207-047-8
• NSC Number: 96637
• UNII: XY6HY5ZM28
• DSSTox Substance ID: DTXSID601311832
• Nikkaji Number: J196.107A
• Wikidata: Q27294053
• ChEMBL ID: CHEMBL1602552
• Mol file: 427-49-6.mol

Synonyms:427-49-6;alpha-Cyclopentylmandelic acid;2-cyclopentyl-2-hydroxy-2-phenylacetic acid;Cyclopentylphenylglycolic acid;Cyclopentyl-hydroxy-phenyl-acetic acid;cyclopentyl(hydroxy)phenylacetic acid;cyclopentylmandelic acid;UNII-XY6HY5ZM28;XY6HY5ZM28;alpha-Cyclopentyl-DL-mandelic Acid;EINECS 207-047-8;MFCD00019296;NSC-96637;A-Cyclo Pentyl Mandelic Acid;2-(RS)-Cyclopentyl-2-hydroxy-2-phenylacetic Acid (alpha-Cyclopentylmandelic Acid);Cyclopentyl Mandelic Acid;cyclopentyl-mandelic acid;2-Cyclopentyl mandelic acid;Oprea1_794057;phenylcyclopentylglycolic acid;(-)-cyclopentylmandelic acid;MLS000036193;SCHEMBL415801;alpha -Cyclopentylmandelic acid;racemic cyclopentylmandelic acid;CHEMBL1602552;Mandelic acid, alpha-cyclopentyl;DTXSID601311832;HMS2321I07;Cyclopentylhydroxy-phenylacetic acid;NSC96637;alpha-Cyclopentylmandelic acid, 97%;BBL008864;NSC 96637;STK506752;AKOS003238403;AKOS016342184;CS-W014250;(+/-)-CYCLOPENTYLMANDELIC ACID;.ALPHA.-CYCLOPENTYLMANDELIC ACID;AC-16192;AS-65728;SMR000034062;SY011589;AM20040451;BB 0241799;C2394;FT-0622135;2-cyclopentyl-2-hydroxy-2-phenyl acetic acid;EN300-6497662;.ALPHA.-CYCLOPENTYLMANDELIC ACID, (+/-)-;SR-01000322777;SR-01000322777-1;W-106263;2-CYCLOPENTYL-2-HYDROXY-2-(PHENYL)ACETIC ACID;GLYCOPYRRONIUM BROMIDE IMPURITY J [EP IMPURITY];Q27294053;Z2044818613;BENZENEACETIC ACID, .ALPHA.-CYCLOPENTYL-.ALPHA.-HYDROXY-;2-Cyclopentyl-2-hydroxy-2-phenylacetic acid

Chemical Property of alpha-Cyclopentylmandelic acid

Chemical Property:

• Appearance/Colour: white to beige powder
• Vapor Pressure: 5.73E-07mmHg at 25°C
• Melting Point: 144-150 °C
• Boiling Point: 395.6 °C at 760 mmHg
• PKA: 3.53±0.25(Predicted)
• Flash Point: 207.2 °C
• PSA: 57.53000
• Density: 1.247 g/cm³
• LogP: 2.14900
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 220.109944368
• Heavy Atom Count: 16
• Complexity: 252

Purity/Quality:

99%, ^*data from raw suppliers

2-Cyclopentyl-2-hydroxy-2-phenylaceticAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C,Xi
• Hazard Codes: C,Xi
• Statements: 34-41-37/38
• Safety Statements: 45-36/37/39-26-39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1CCC(C1)C(C2=CC=CC=C2)(C(=O)O)O
• Uses: intermediate for Glycopyrronium Bromide, Oxyphencyclimine HCl, Oxypyrronium Bromide 2-Cyclopentyl-2-hydroxy-2-phenylacetic Acid is an impurity of Glycopyrrolate (G657000), a novel pharmaceutical compound based on PDE IV inhibitors; used in the treatment of respiratory complaints. It is used in the synthesis of muscarinic M3 receptor antagonists.

Technology Process of alpha-Cyclopentylmandelic acid

There total 9 articles about alpha-Cyclopentylmandelic 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: 92.0%

glycopyrronium bromide (596-51-0,129784-12-9,201667-20-1,53808-86-9,58493-54-2) → 3-hydroxy-1,1-dimethyl pyrrolidinium bromide (51052-74-5) + 2-cyclopentyl-2-hydroxy-2-phenylacetic acid (427-49-6)

Guidance literature:

With sodium hydroxide; In water; at 20 ℃;

Reference yield: 36.4%

Benzoylformic acid (611-73-4) + cyclopentylmagnesium bromide (33240-34-5) → 2-cyclopentyl-2-hydroxy-2-phenylacetic acid (427-49-6)

Guidance literature:

In diethyl ether; at 0 - 20 ℃; for 24.5h;

Reference yield: 25.0%

2-Cyclopentyl-2-hydroxy-2-phenylacetic acid methyl ester (19833-96-6) → 2-cyclopentyl-2-hydroxy-2-phenylacetic acid (427-49-6)

Guidance literature:

With sodium hydroxide; In methanol; water; at 20 ℃; Inert atmosphere;

DOI:10.1021/op3001788

upstream raw materials:

Benzoylformic acid

cyclopentylmagnesium bromide

Cyclozil chloromethacryloyloxymethylate

2-cyclopentyl-2-hydroxy-2-phenylacetic acid ethyl ester

Downstream raw materials:

(1α, 5α ,6α)-6-N-(3-azabicyclo[3.1.0] hexyl-3-benzyl)-2-cyclopentyl-2-hydroxy-2-phenyl acetamide

2-cyclopentylidene-1-phenylacetic acid

3-(2-cyclopentylidene-2-phenylacetoxy)-1,1-dimethylpyrrolidinium bromide

1-benzyl-3-(2-cyclopentyl-2-hydroxy-2-phenylacetoxy)-1-methylpyrrolidinium bromide

Refernces

• 1、 -. "GLYCOPYRRONIUM FATTY ACID SALTS AND METHODS OF MAKING SAME". Paragraph 59. . Retrieved 2017/01/02.
• 2、 Wu,Wu,Mori,Buchwald,Bodor, Nicholas. "Stereoisomers of N-substituted soft anticholinergics and their zwitterionic metabolite based on glycopyrrolate - Syntheses and pharmacological evaluations". experimental part. p. 200 - 209. Retrieved 2009/04/07.