(S)-1-Tert-butyl 2-methyl 4-oxopyrrolidine-1,2-dicarboxylate

Base Information

• Chemical Name: (S)-1-Tert-butyl 2-methyl 4-oxopyrrolidine-1,2-dicarboxylate
• CAS No.: 102195-80-2
• Molecular Formula: C11H17NO5
• Molecular Weight: 243.26
• Hs Code.: 29339900
• European Community (EC) Number: 625-165-1
• DSSTox Substance ID: DTXSID70450972
• Nikkaji Number: J1.749.976I
• Wikidata: Q72450236
• Mol file: 102195-80-2.mol

Synonyms:102195-80-2;Boc-4-Oxo-Pro-OMe;N-Boc-4-oxo-L-proline methyl ester;(S)-1-TERT-BUTYL 2-METHYL 4-OXOPYRROLIDINE-1,2-DICARBOXYLATE;1-tert-butyl 2-methyl (2S)-4-oxopyrrolidine-1,2-dicarboxylate;MFCD01861778;1-O-tert-butyl 2-O-methyl (2S)-4-oxopyrrolidine-1,2-dicarboxylate;1,2-Pyrrolidinedicarboxylic acid, 4-oxo-, 1-(1,1-dimethylethyl) 2-methyl ester, (2S)-;N-Boc-4-oxo-L-prolinemethylester;SCHEMBL719488;BOC-L-PRO(4-KETO)-OME;DTXSID70450972;UPBHYYJZVWZCOZ-QMMMGPOBSA-N;AM676;N-Boc-4-oxo-proline methyl ester;METHYL 1-BOC-4-OXO-PROLINE;(2S)-4-Oxo-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid methyl ester;AKOS015850934;O1-TERT-BUTYL O2-METHYL (2S)-4-OXOPYRROLIDINE-1,2-DICARBOXYLATE;CS-W001280;GS-6425;AC-22994;N-Boc-4-oxo-L-proline methyl ester, 97%;1-BOC-4-OXO-L-PROLINE METHYL ESTER;A5156;N-(BOC)-4-oxo-(L)-proline, methyl ester;N-t-butoxycarbonyl-4-oxoproline methyl ester;EN300-342771;M03317;N-t-butoxycarbonyl-4-oxo-L-proline methyl ester;A800539;(S)-2-Methyl 1-Boc-4-oxopyrrolidine-2-carboxylate;J-502379;W-206967;1-(tert-Butoxycarbonyl)-4-oxo-L-proline methyl ester;(S)-4-Oxo-N-Boc-pyrrolidine-2-carboxylic Acid Methyl Ester;1-tert-butyl 2-methyl (2S)-4-oxo-1,2-pyrrolidinedicarboxylate;1-tert-butyl 2-methyl (2s)-4oxo-1,2-pyrrolidinedicarboxylate;1-tert-butyl 2-methyl(2s)-4-oxopyrrolidine-1,2-dicarboxylate;(S)-1-TERT-BUTYL2-METHYL4-OXOPYRROLIDINE-1,2-DICARBOXYLATE;1-tert-butyl 2-methyl (25)-4-oxo-1,2-pyrrolidinedicarboxylate;tert-Butyl (2S)-2-(Methoxycarbonyl)-4-oxopyrrolidine-1-carboxylate;O1-tert-butyl O2-methyl (2S)-4-oxidanylidenepyrrolidine-1,2-dicarboxylate;(2S)-4-oxopyrrolidine-1,2-dicarboxylic acid O1-tert-butyl ester O2-methyl ester;(S)-4-OXO-PYRROLIDINE-1,2-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER 2-METHYL ESTER;(S)-1-tert-butyl 2-methyl 4-oxopyrrolidine-1,2-dicarboxylate

Chemical Property of (S)-1-Tert-butyl 2-methyl 4-oxopyrrolidine-1,2-dicarboxylate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 35-40 °C
• Refractive Index: 1.488
• Boiling Point: 333.149 °C at 760 mmHg
• PKA: -3.86±0.40(Predicted)
• Flash Point: 155.283 °C
• PSA: 72.91000
• Density: 1.21 g/cm³
• LogP: 0.67580
• Storage Temp.: ?20°C
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 243.11067264
• Heavy Atom Count: 17
• Complexity: 344

Purity/Quality:

99% ^*data from raw suppliers

(2S)-1-Boc-4-oxo-prolineMethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22-41
• Safety Statements: 26-36/37-39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1CC(=O)CC1C(=O)OC
• Isomeric SMILES: CC(C)(C)OC(=O)N1CC(=O)C[C@H]1C(=O)OC
• Uses: (2S)-1-Boc-4-oxo-proline Methyl Ester (cas# 102195-80-2) is a compound useful in organic synthesis.

Technology Process of (S)-1-Tert-butyl 2-methyl 4-oxopyrrolidine-1,2-dicarboxylate

There total 21 articles about (S)-1-Tert-butyl 2-methyl 4-oxopyrrolidine-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) → (S)-1-tert-butyl 2-methyl 4-oxopyrrolidine-1,2-dicarboxylate (102195-80-2)

Guidance literature:

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -78 - 0 ℃;

DOI:10.1248/cpb.48.740

Reference yield: 100.0%

trans-4-hydroxy-L-BOC-proline → (S)-1-tert-butyl 2-methyl 4-oxopyrrolidine-1,2-dicarboxylate (102195-80-2)

Guidance literature:

trans-4-hydroxy-L-BOC-proline; With oxalyl dichloride; In dichloromethane; dimethyl sulfoxide; at -78 - -50 ℃; for 4.25h;

With triethylamine; In dichloromethane; dimethyl sulfoxide; at 20 ℃;

Reference yield: 93.0%

(2S,4S)-N-tert-butoxycarbonyl-4-hydroxyproline methyl ester (74844-91-0,114676-69-6,135042-17-0,227935-38-8,102195-79-9) → (S)-1-tert-butyl 2-methyl 4-oxopyrrolidine-1,2-dicarboxylate (102195-80-2)

Guidance literature:

With sodium periodate; ruthenium tetroxide; In tetrachloromethane; chloroform; at 0 ℃; for 1.5h;

DOI:10.1055/s-1986-31487

upstream raw materials:

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

(2S,4S)-N-tert-butoxycarbonyl-4-hydroxyproline methyl ester

di-tert-butyl dicarbonate

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

Downstream raw materials:

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

(-)-kainic acid

(2S)-1-(tert-butoxycarbonyl)-4-ethylpyrrolidine-2-carboxylic acid

C₄₇H₅₆F₄N₄O₁₂

Refernces

• 1、 Yoshifuji,Kaname. "Asymmetric synthesis of lycoperdic acid". . p. 1617 - 1620. Retrieved 1995.
• 2、 Dormoy, Jean-Robert,Castro, Bertrand. "Synthesis of N-t-Butoxycarbonyl-4,4-dideuterio-L-proline". . p. 81 - 82. Retrieved 1986.
• 3、 -. "NOVEL CONNECTED BODY AND USE THEREOF IN SPECIFIC CONJUGATION BETWEEN BIOMOLECULE AND DRUG". Paragraph 0211-0212. . Retrieved 2021/05/14.
• 4、 -. "Pyrimidine derivative and application thereof in medicines". Paragraph 0251-0254. . Retrieved 2021/07/21.