(2S,4R)-1-tert-Butyl 2-methyl 4-((methylsulfonyl)oxy)pyrrolidine-1,2-dicarboxylate

Base Information

• Chemical Name: (2S,4R)-1-tert-Butyl 2-methyl 4-((methylsulfonyl)oxy)pyrrolidine-1,2-dicarboxylate
• CAS No.: 84520-67-2
• Molecular Formula: C12H21 N O7 S
• Molecular Weight: 323.367
• DSSTox Substance ID: DTXSID00563867
• Nikkaji Number: J1.659.663I
• Wikidata: Q82448363
• Mol file: 84520-67-2.mol

Synonyms:84520-67-2;(2S,4R)-1-tert-Butyl 2-methyl 4-((methylsulfonyl)oxy)pyrrolidine-1,2-dicarboxylate;(2S, 4R)-Boc-gamma-MsO-proline methyl ester;(2S,4R)-BOC-GAMMA-MSO-PROLINE METHYL ESTER;1-O-tert-butyl 2-O-methyl (2S,4R)-4-methylsulfonyloxypyrrolidine-1,2-dicarboxylate;(2S,4R)-1-TERT-BUTYL 2-METHYL 4-(METHYLSULFONYLOXY)PYRROLIDINE-1,2-DICARBOXYLATE;C12H21NO7S;QXGDJXLJHBZELB-BDAKNGLRSA-N;SCHEMBL489252;DTXSID00563867;MFCD04115796;AKOS015999230;(2S,4R)-1-tert-Butyl2-methyl4-((methylsulfonyl)oxy)pyrrolidine-1,2-dicarboxylate;(3R,5S)-1-(tert-butoxycarbonyl)-5-(methoxycarbonyl)pyrrolidin-3-yl methanesulfonate;AS-11204;BP-11819;CS-0154799;(2S,4R)-Boc-gamma-mso-prolione methyl ester;(2S,4R)-BOC-GAMMA-MSO-PROLINEMETHYLESTER;A864114;Trans-N-Boc-4-methanesulfonyloxy-L-proline Methyl Ester;(2S,4R)-1-Boc-2-methyl 4-((methylsulfonyl)oxy)pyrrolidine-2-carboxylate;(2S,4R)-1-t-butoxycarbonyl-4-methylsulfonyloxy-2-methoxycarbonylpyrrolidine;(2S,4R)-N-tert-butoxycarbonyl-4-methanesulfonyloxyproline methyl ester;Methyl (2S,4R)-1-Boc-4-[(methylsulfonyl)oxy]pyrrolidin-2-carboxylate;methyl (2S,4R)-1-Boc-4-[(methylsulfonyl)oxy]pyrrolidine-2-carboxylate;Methyl(2S,4R)-1-Boc-4-[(methylsulfonyl)oxy]pyrrolidin-2-carboxylate;(2S, 4R)-1-(t-butoxycarbonyl)-4-methanesulfonyloxy-2-methoxycarbonylpyrrolidine;(2S,4R)-1-t-butoxycarbonyl-4-methanesulfonyloxypyrrolidine-2-carboxylic acid methyl ester;(2S,4R)-1-tert-Butyl 2-methyl 4-((methylsulfonyl)-oxy)pyrrolidine-1,2-dicarboxylate;(4R)-1-(tert-butyloxycarbonyl)-4-(methane-sulfonyloxy)-L-proline methyl ester;1-(tert-butyl) 2-methyl (2S,4R)-4-((methylsulfonyl)oxy)pyrrolidine-1,2-dicarboxylate;1-tert-Butyl 2-methyl (2S,4R)-4-[(methanesulfonyl)oxy]pyrrolidine-1,2-dicarboxylate;1-tert-butyl(2s,4r) 2-methyl 4-[(methylsulfonyl)oxy]pyrrolidine-1,2-dicarboxylate;Methyl (2S,4R)-N-tert-butoxycarbonyl-4-methane-sulfonyloxypyrrolidine-2-carboxylate;methyl (2S,4R)-N-tert-butoxycarbonyl-4-methanesulfonyloxypyrrolidine-2-carboxylate;(2S,4R)-4-(methylsulfonyloxy)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butylester-2-methylester;(2S,4R)-4-Methanesulfonyloxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester;(2S,4R)-4-methanesulfonyloxypyrrolidine-1,2-dicarboxylic Acid 1-t-Butyl Ester 2-Methyl Ester

Chemical Property of (2S,4R)-1-tert-Butyl 2-methyl 4-((methylsulfonyl)oxy)pyrrolidine-1,2-dicarboxylate

Chemical Property:

• Melting Point: 82-85 °C
• Boiling Point: 443.6 °C at 760 mmHg
• PKA: -5.72±0.60(Predicted)
• Flash Point: 222.1 °C
• PSA: 107.59000
• Density: 1.3 g/cm³
• LogP: 1.53230
• Storage Temp.: 2-8°C
• Water Solubility.: at 25 deg C (mg/L): 1251
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 6
• Exact Mass: 323.10387318
• Heavy Atom Count: 21
• Complexity: 503

Purity/Quality:

99% ^*data from raw suppliers

(2S,4R)-Boc-γ-mso-prolinemethylester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1CC(CC1C(=O)OC)OS(=O)(=O)C
• Isomeric SMILES: CC(C)(C)OC(=O)N1C[C@@H](C[C@H]1C(=O)OC)OS(=O)(=O)C
• Uses: (2S,4R)-Boc-gamma-mso-proline methyl ester

Technology Process of (2S,4R)-1-tert-Butyl 2-methyl 4-((methylsulfonyl)oxy)pyrrolidine-1,2-dicarboxylate

There total 17 articles about (2S,4R)-1-tert-Butyl 2-methyl 4-((methylsulfonyl)oxy)pyrrolidine-1,2-dicarboxylate 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: 100.0%

1-tert-butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate (74844-91-0) + methanesulfonyl chloride (124-63-0) → (2S,4R)-4-(methylsulfonyloxy)pyrrolidine-1,2-dicarboxylic acid 1-tert-butylester-2-methylester (84520-67-2)

Guidance literature:

With triethylamine; In tetrahydrofuran; for 0.5h; Cooling with ice;

Reference yield: 90.0%

(2R,4S)-1-tert-butyl 2-methyl 4-hydroxypyrrolidine-1,2-dicarboxylate (135042-17-0) + methanesulfonyl chloride (124-63-0) → (2S,4R)-4-(methylsulfonyloxy)pyrrolidine-1,2-dicarboxylic acid 1-tert-butylester-2-methylester (84520-67-2)

Guidance literature:

With triethylamine; In dichloromethane; at 0 - 20 ℃;

Reference yield: 85.0%

→ (2S,4R)-4-(methylsulfonyloxy)pyrrolidine-1,2-dicarboxylic acid 1-tert-butylester-2-methylester (84520-67-2)

Guidance literature:

upstream raw materials:

1-tert-butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate

methanesulfonyl chloride

(R)-4-hydroxy-L-proline ethyl ester

4R-4-hydroxyproline

Downstream raw materials:

N-BOC-3,4-didehydro-(S)-proline methyl ester

1-tert-butyl 2-methyl (2S,4S)-4-fluoropyrrolidine-1,2-dicarboxylate

N-Boc-cAmp-Leu-Phe-OMe

N-Boc-cAmp(Boc)-Leu-Phe-OMe

Refernces

• 1、 Myers, Eddie L.,Palte, Michael J.,Raines, Ronald T.. "Catalysis of Hydrogen-Deuterium Exchange Reactions by 4-Substituted Proline Derivatives". . p. 1247 - 1256. Retrieved 2019.
• 2、 Hajduch, Jan,Fabre, Benjamin,Klopp, Benjamin,Pohl, Radek,Budě?ínsky, Milo?,?olínová, Veronika,Ka?i?ka, Václav,K?prülüoglu, Cemal,Eyrilmez, Saltuk Mustafa,Lep?ík, Martin,Hobza, Pavel,Mitrová, Katarína,Lubos, Marta,Hernández, María Soledad Garre,Jirá?ek, Ji?í. "Multipodal insulin mimetics built on adamantane or proline scaffolds". . . Retrieved 2020/12/29.
• 3、 -. "TRI-SUBSTITUTED HETEROARYL DERIVATIVES AS SRC HOMOLOGY-2 PHOSPHATASE INHIBITORS". Page/Page column 141. . Retrieved 2020/04/25.