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

Base Information

• Chemical Name: Methyl (2S,4S)-1-(tert-butoxycarbonyl)-4-methylpyroglutamate
• CAS No.: 196394-48-6
• Molecular Formula: C12H19NO5
• Molecular Weight: 257.287
• DSSTox Substance ID: DTXSID90450171
• Wikidata: Q82269768
• Mol file: 196394-48-6.mol

Synonyms:196394-48-6;Methyl (2S,4S)-1-(tert-butoxycarbonyl)-4-methylpyroglutamate;1-O-tert-butyl 2-O-methyl (2S,4S)-4-methyl-5-oxopyrrolidine-1,2-dicarboxylate;(2S,4S)-1-tert-Butyl 2-methyl 4-methyl-5-oxopyrrolidine-1,2-dicarboxylate;1-(tert-Butyl) 2-methyl (2S,4S)-4-methyl-5-oxopyrrolidine-1,2-dicarboxylate;1393537-75-1;starbld0002576;SCHEMBL2601624;DTXSID90450171;YTLCHNBFNGFDSD-YUMQZZPRSA-N;J-012689

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

Chemical Property:

• PSA: 72.91000
• LogP: 1.26940
• Solubility.: Dichloromethane, Ethyl Acetate, Methanol
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 257.12632271
• Heavy Atom Count: 18
• Complexity: 371

Purity/Quality:

97% ^*data from raw suppliers

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

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CC(N(C1=O)C(=O)OC(C)(C)C)C(=O)OC
• Isomeric SMILES: C[C@H]1C[C@H](N(C1=O)C(=O)OC(C)(C)C)C(=O)OC
• Uses: Methyl (2S,4S)-1-(tert-butoxycarbonyl)-4-methylpyroglutamate (cas# 196394-48-6) is a compound useful in organic synthesis.

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

There total 12 articles about Methyl (2S,4S)-1-(tert-butoxycarbonyl)-4-methylpyroglutamate 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%

methyl (S)-1-tert-butoxycarbonyl-3-[(E)-(dimethylamino)methylidene]-2-pyrrolidinone-5-carboxylate (219844-08-3) → (2S,4S)-1-tert-butyl 2-methyl 4-methyl-5-oxopyrrolidine-1,2-dicarboxylate (196394-48-6)

Guidance literature:

With hydrogen; 5%-palladium/activated carbon; In isopropyl alcohol; at 45 ℃; for 18h; under 2327.23 Torr;

Reference yield:

(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) + (2S,4R)-1-(tert-butyl) 2-methyl 4-methyl-5-oxopyrrolidine-1,2-dicarboxylate (196394-49-7) + (2S,4S)-1-tert-butyl 2-methyl 4-methyl-5-oxopyrrolidine-1,2-dicarboxylate (196394-48-6)

Guidance literature:

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

methyl iodide; In tetrahydrofuran; at -78 ℃;

DOI:10.1016/S0040-4039(03)00429-5

Reference yield:

methyl (S)-1-tert-butoxycarbonyl-3-[(E)-(dimethylamino)methylidene]-2-pyrrolidinone-5-carboxylate (219844-08-3) → (2S,4R)-1-(tert-butyl) 2-methyl 4-methyl-5-oxopyrrolidine-1,2-dicarboxylate (196394-49-7) + (2S,4S)-1-tert-butyl 2-methyl 4-methyl-5-oxopyrrolidine-1,2-dicarboxylate (196394-48-6)

Guidance literature:

With hydrogen; 5%-palladium/activated carbon; In isopropyl alcohol; at 45 ℃; for 18h; under 2327.23 Torr;

upstream raw materials:

methyl (S)-1-tert-butoxycarbonyl-3-[(E)-(dimethylamino)methylidene]-2-pyrrolidinone-5-carboxylate

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

methyl iodide

methyl (S)-pyroglutamate

Downstream raw materials:

C₂₀H₂₄BrN₃O₂

C₂₀H₂₄BrNO₅

C₁₉H₂₄BrN₃O₂

(2-(2-(4-bromophenyl)-2-oxoethyl)) 1-(tert-butyl) (2S,4S)-4-methylpyrrolidine-1,2-dicarboxylate