1-[(4-Methoxyphenyl)sulfonyl]-cis-4-hydroxy-D-proline

Base Information

• Chemical Name: 1-[(4-Methoxyphenyl)sulfonyl]-cis-4-hydroxy-D-proline
• CAS No.: 203994-66-5
• Molecular Formula: C12H15NO6S
• Molecular Weight: 301.32
• DSSTox Substance ID: DTXSID10368628
• Wikidata: Q82155317
• Mol file: 203994-66-5.mol

Synonyms:203994-66-5;(2R,4R)-4-Hydroxy-1-((4-methoxyphenyl)sulfonyl)pyrrolidine-2-carboxylic acid;AC1M6VJW;SCHEMBL8210480;1-[(4-Methoxyphenyl)sulfonyl]-cis-4-hydroxy-D-proline;DTXSID10368628;YBWUYYVFHIGKPL-LDYMZIIASA-N;AKOS017509970

Chemical Property of 1-[(4-Methoxyphenyl)sulfonyl]-cis-4-hydroxy-D-proline

Chemical Property:

• XLogP3: 0.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 4
• Exact Mass: 301.06200837
• Heavy Atom Count: 20
• Complexity: 451

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC=C(C=C1)S(=O)(=O)N2CC(CC2C(=O)O)O
• Isomeric SMILES: COC1=CC=C(C=C1)S(=O)(=O)N2C[C@@H](C[C@@H]2C(=O)O)O

Technology Process of 1-[(4-Methoxyphenyl)sulfonyl]-cis-4-hydroxy-D-proline

There total 1 articles about 1-[(4-Methoxyphenyl)sulfonyl]-cis-4-hydroxy-D-proline 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:

4-methoxy-phenyl-sulphonyl chloride (98-68-0) + cis-hydroxy-D-proline (2584-71-6,30724-02-8) → (2R,4R)-4-Hydroxy-1-(4-methoxy-benzenesulfonyl)-pyrrolidine-2-carboxylic acid (203994-66-5)

Guidance literature:

With dmap; triethylamine; In 1,4-dioxane; water; at 20 ℃; for 14h;

DOI:10.1021/jm9904699

Reference yield:

(2R,4R)-4-Hydroxy-1-(4-methoxy-benzenesulfonyl)-pyrrolidine-2-carboxylic acid (203994-66-5) → (R)-1-(4-Methoxy-benzenesulfonyl)-4-oxo-pyrrolidine-2-carboxylic acid

Guidance literature:

With jones reagent; In acetone; at 20 ℃; for 14h;

DOI:10.1021/jm9904699

Reference yield:

(2R,4R)-4-Hydroxy-1-(4-methoxy-benzenesulfonyl)-pyrrolidine-2-carboxylic acid (203994-66-5) → (2R,4S)-1-(4-Methoxy-benzenesulfonyl)-4-piperidin-1-yl-pyrrolidine-2-carboxylic acid methyl ester (204072-88-8)

Guidance literature:

Multi-step reaction with 5 steps

1: SOCl₂ / 14 h

2: Et₃N / CH₂Cl₂ / 20 °C

3: 79 percent / NaN₃ / dimethylformamide / 26 h / 55 °C

4: 58 percent / H₂; HCOOH / 10percent Pd/C / ethanol; tetrahydrofuran / 16 h / 2792.67 Torr

5: Et₃N / dimethylformamide / 3 h / 60 °C

With formic acid; thionyl chloride; sodium azide; hydrogen; triethylamine; 10percent Pd/C; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm000246e

upstream raw materials:

4-methoxy-phenyl-sulphonyl chloride

cis-hydroxy-D-proline

Downstream raw materials:

1N-(4-methoxybenzenesulfonyl)-2(R)-carbomethoxy-4(R)-hydroxypyrrolidine

1N-(4-methoxybenzenesulfonyl)-2(R)-carbomethoxy-4(S)-aminopyrrolidine

1N-(4-methoxybenzenesulfonyl)-2(R)-carbomethoxy-4(S)-azidopyrrolidine

1N-(4-methoxybenzenesulfonyl)-2(R)-carbomethoxy-4(R)-methanesulfonyloxypyrrolidine

Refernces

• 1、 Cheng, Menyan,De, Biswanath,Almstead, Neil G.,Pikul, Stanislaw,Dowty, Martin E.,Dietsch, Charles R.,Dunaway, C. Michelle,Gu, Fei,Hsieh, Lily C.,Janusz, Michael J.,Taiwo, Yetunde O.,Natchus, Michael G.,Hudlicky, Tomas,Mandel, Martin. "Design, synthesis, and biological evaluation of matrix metalloproteinase inhibitors derived from a modified proline scaffold". . p. 5426 - 5436. Retrieved 2007/10/03.