Methyl (2S)-1-(tert-butoxycarbonyl)-4,4-dimethylpyroglutamate

Base Information

• Chemical Name: Methyl (2S)-1-(tert-butoxycarbonyl)-4,4-dimethylpyroglutamate
• CAS No.: 158392-74-6
• Molecular Formula: C₁₃H₂₁NO₅
• Molecular Weight: 271.313
• Mol file: 158392-74-6.mol

Synonyms:1,2-Pyrrolidinedicarboxylicacid, 4,4-dimethyl-5-oxo-, 1-(1,1-dimethylethyl) 2-methyl ester, (S)-

Chemical Property of Methyl (2S)-1-(tert-butoxycarbonyl)-4,4-dimethylpyroglutamate

Chemical Property:

• Refractive Index: 1.473
• Boiling Point: 369.4±35.0 °C(Predicted)
• PKA: -4.19±0.60(Predicted)
• PSA: 72.91000
• Density: 1.132±0.06 g/cm3(Predicted)
• LogP: 1.65950
• Solubility.: Dichloromethane, Ethyl Acetate, Methanol

Purity/Quality:

97% ^*data from raw suppliers

Methyl(2S)-1-(tert-butoxycarbonyl)-4,4-dimethylpyroglutamate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Methyl (2S)-1-(tert-butoxycarbonyl)-4,4-dimethylpyroglutamate (cas# 158392-74-6) is a compound useful in organic synthesis.

Technology Process of Methyl (2S)-1-(tert-butoxycarbonyl)-4,4-dimethylpyroglutamate

There total 7 articles about Methyl (2S)-1-(tert-butoxycarbonyl)-4,4-dimethylpyroglutamate 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: 51.07%

(S)-1-tert-butoxycarbonyl-5-methoxycarbonyl-pyrrolidin-2-one (108963-96-8) + methyl trifluoromethanesulfonate (333-27-7) → O1-tert-butyl O2-methyl (2S)-4,4-dimethyl-5-oxopyrrolidine-1,2-dicarboxylate (158392-74-6)

Guidance literature:

(S)-1-tert-butoxycarbonyl-5-methoxycarbonyl-pyrrolidin-2-one; With lithium hexamethyldisilazane; In toluene; at -70 ℃; for 1h; Inert atmosphere;

methyl trifluoromethanesulfonate; In toluene; at -70 ℃; for 6h;

Reference yield: 38.4%

(S)-1-tert-butoxycarbonyl-5-methoxycarbonyl-pyrrolidin-2-one (108963-96-8) + methyl iodide (74-88-4) → O1-tert-butyl O2-methyl (2S)-4,4-dimethyl-5-oxopyrrolidine-1,2-dicarboxylate (158392-74-6)

Guidance literature:

(S)-1-tert-butoxycarbonyl-5-methoxycarbonyl-pyrrolidin-2-one; With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 0.5h; Inert atmosphere;

methyl iodide; In tetrahydrofuran; at -78 - 20 ℃; for 1h; Inert atmosphere;

DOI:10.1021/acs.jmedchem.1c01171

Reference yield:

(S)-1-tert-butoxycarbonyl-5-methoxycarbonyl-pyrrolidin-2-one (108963-96-8) → O1-tert-butyl O2-methyl (2S)-4,4-dimethyl-5-oxopyrrolidine-1,2-dicarboxylate (158392-74-6)

Guidance literature:

(S)-1-tert-butoxycarbonyl-5-methoxycarbonyl-pyrrolidin-2-one; Me-X; With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃;

Me-X; With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃;

DOI:10.1016/j.bmcl.2013.01.094

upstream raw materials:

(S)-1-tert-butoxycarbonyl-5-methoxycarbonyl-pyrrolidin-2-one

methyl iodide

methyl (S)-pyroglutamate

L-Pyroglutamic acid

Downstream raw materials:

(2S)-1-(tert-butoxycarbonyl)-4,4-dimethylpyrrolidine-2-carboxylic acid

C₁₉H₂₃ClN₆O₂

C₂₀H₂₅ClN₆O₂

C₂₁H₂₇ClN₆O₂

Refernces

• 1、 -. "INHIBITORS OF CYCLIN-DEPENDENT KINASE 7 (CDK7)". Paragraph 125. . Retrieved 2020/05/28.
• 2、 -. "COMPOUNDS, COMPOSITIONS AND METHODS FOR SYNTHESIS". Paragraph 001535; 001536; 001537; 001538. . Retrieved 2019/01/10.