N-Boc-trans-4-tosyloxy-L-proline methyl ester

Base Information

• Chemical Name: N-Boc-trans-4-tosyloxy-L-proline methyl ester
• CAS No.: 88043-21-4
• Molecular Formula: C18H25 N O7 S
• Molecular Weight: 413.492
• Hs Code.: 2933990090
• Mol file: 88043-21-4.mol

Synonyms:1,2-Pyrrolidinedicarboxylicacid, 4-[[(4-methylphenyl)sulfonyl]oxy]-, 1-(1,1-dimethylethyl) 2-methyl ester,(2S-trans)-; tert-Butyl methyl(2S,4R)-4-[[(4-methylphenyl)sulfonyl]oxy]pyrrolidine-1,2-dicarboxylate

Chemical Property of N-Boc-trans-4-tosyloxy-L-proline methyl ester

Chemical Property:

• Melting Point: 77.0 to 81.0 °C
• Boiling Point: 520.5 °C at 760 mmHg
• Flash Point: 268.6 °C
• PSA: 107.59000
• Density: 1.265 g/cm³
• LogP: 3.27000
• Storage Temp.: 2-8°C
• Solubility.: Chloroform

Purity/Quality:

99.9% ^*data from raw suppliers

trans-N-tert-Butyloxycarbonyl-4-tosyloxy-L-prolineMethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Uses: N-Boc-trans-4-tosyloxy-L-proline methyl ester is used in the preparation of bicycloazahydantoins, as androgen receptor antagonists

Technology Process of N-Boc-trans-4-tosyloxy-L-proline methyl ester

There total 9 articles about N-Boc-trans-4-tosyloxy-L-proline methyl ester 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: 99.0%

1-tert-butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate (74844-91-0) + p-toluenesulfonyl chloride (98-59-9) → (2S,4R)-4-(toluene-4-sulfonyloxy)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (88043-21-4)

Guidance literature:

With pyridine; In dichloromethane;

DOI:10.1016/j.bmcl.2004.09.049

Reference yield: 88.0%

(2S,4R)-methyl-4-hydroxypyrrolidine-2-carboxylate hydrochloride (144527-44-6) + p-toluenesulfonyl chloride (98-59-9) → (2S,4R)-4-(toluene-4-sulfonyloxy)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (88043-21-4)

Guidance literature:

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

DOI:10.1002/anie.201302014

Reference yield: 56.5%

1-tert-butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate (74844-91-0) + methyl p-toluene sulfonate (80-48-8) → (2S,4R)-4-(toluene-4-sulfonyloxy)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (88043-21-4)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 0 - 20 ℃; for 5.16667h;

upstream raw materials:

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

p-toluenesulfonyl chloride

1-(t-butoxycarbonyl)-4-hydroxyproline

L-4-hydroxyproline methyl ester hydrochloride

Downstream raw materials:

(2S-trans)-2-hydroxymethyl-4-[[(4-methylphenyl)sulfonyl]oxy]-1-pyrrolidinecarboxylic acid, 1,1-dimethylethyl ester

(2S,4S)-1-(t-butoxycarbonyl)-2-ethoxycarbonyl-4-benzoylthiopyrrolidine

(2S,4S)-4-(4-bromo-phenylsulfanyl)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester

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

Refernces

• 1、 Mendoza, Carolina,de la Croix, Augustin,Riente, Paola,Llorens, Lluís,de Mendoza, Javier,Pericàs, Miquel A.. "Reusable shuttles for exchangeable functional cargos: Reversibly assembled, magnetically powered organocatalysts for asymmetric aldol reactions". supporting information. . Retrieved 2019/09/17.
• 2、 -. "SPIRO-LACTAM AND BIS-SPIRO-LACTAM NMDA RECEPTOR MODULATORS AND USES THEREOF". Page/Page column 68. . Retrieved 2018/03/28.