N-Boc-4-oxo-L-proline

Base Information

• Chemical Name: N-Boc-4-oxo-L-proline
• CAS No.: 84348-37-8
• Molecular Formula: C10H15NO5
• Molecular Weight: 229.233
• Hs Code.: 29339900
• Mol file: 84348-37-8.mol

Synonyms:1,2-Pyrrolidinedicarboxylicacid, 4-oxo-, 1-(1,1-dimethylethyl) ester, (S)-;(2S)-1-(tert-Butoxycarbonyl)-4-oxo-2-pyrrolidinecarboxylicacid;(2S)-1-(tert-Butoxycarbonyl)-4-oxo-2-pyrrolidinecarboxylic acid;1-(tert-Butoxycarbonyl)-4-oxo-L-proline;N-tert-Butoxycarbonyl-4-keto-L-proline;N-tert-Butoxycarbonyl-4-oxo-L-proline;

Chemical Property of N-Boc-4-oxo-L-proline

Chemical Property:

• Vapor Pressure: 0.001Pa at 25℃
• Melting Point: 160 °C (dec.)
• Boiling Point: 390.8±42.0 °C(Predicted)
• PKA: 3.85±0.20(Predicted)
• PSA: 83.91000
• Density: 1.304±0.06 g/cm3(Predicted)
• LogP: 0.58740
• Storage Temp.: Store at 0-5°C
• Water Solubility.: Insoluble in water.

Purity/Quality:

99.9% ^*data from raw suppliers

N-Boc-4-oxo-L-proline ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-36
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Uses: N-Boc-4-oxo-L-proline is used in practical Synthesis of Boc-Protected cis-4-Trifluoromethyl and cis-4-Difluoromethyl-l- prolines.

Technology Process of N-Boc-4-oxo-L-proline

There total 17 articles about N-Boc-4-oxo-L-proline 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: 95.9%

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid (13726-69-7,946610-68-0) → N-tert-butoxycarbonyl-4-oxo-L-proline (84348-37-8)

Guidance literature:

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; trichloroisocyanuric acid; In ethyl acetate; at -5 - 30 ℃; for 1.33333h;

Reference yield: 91.0%

di-tert-butyl dicarbonate (24424-99-5) + 4R-4-hydroxyproline (51-35-4,30724-02-8) → N-tert-butoxycarbonyl-4-oxo-L-proline (84348-37-8)

Guidance literature:

di-tert-butyl dicarbonate; 4R-4-hydroxyproline; With sodium hydrogencarbonate; In 1,4-dioxane; water; at 0 - 20 ℃;

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; trichloroisocyanuric acid; In dichloromethane; at 0 - 20 ℃; for 1h;

Reference yield: 90.0%

2-benzyl 1-(tert-butyl) (S)-4-oxopyrrolidine-1,2-dicarboxylate (154456-97-0) → N-tert-butoxycarbonyl-4-oxo-L-proline (84348-37-8)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethyl acetate; for 24h;

DOI:10.1016/0040-4020(95)00135-U

upstream raw materials:

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

N-tert-butoxycarbonyl-L-cis-4-hydroxyproline

2-benzyl 1-(tert-butyl) (S)-4-oxopyrrolidine-1,2-dicarboxylate

di-tert-butyl dicarbonate

Downstream raw materials:

N-tert-butoxycarbonyl-L-cis-4-hydroxyproline

N-(tert-butyloxycarbonyl)-trans-4-(methylthio)-L-proline

(2S,4R)-2-[(S)-1-((S)-1-Methoxycarbonyl-2-phenyl-ethylcarbamoyl)-3-methyl-butylcarbamoyl]-4-methylsulfanyl-pyrrolidine-1-carboxylic acid tert-butyl ester

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

Refernces

• 1、 -. "Method for synthesizing tert-2-(3- (2S)-4- butyl)-1- ester of n-oxo-isothiazole alkyloxycarbonylpyrrolidinecarboxylic acid (by machine translation)". Paragraph 0038; 0041-0042; 0053; 0056-0057; 0066; 0069-0070. . Retrieved 2020/02/14.
• 2、 -. "Industrial production method of teneligptin intermediate". Paragraph 0023-0028; 0034-0039; 0045-0050; 0056-0061. . Retrieved 2019/04/04.