(R)-4-OXO-PYRROLIDINE-1,2-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER

Base Information

• Chemical Name: (R)-4-OXO-PYRROLIDINE-1,2-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER
• CAS No.: 364077-84-9
• Molecular Formula: C10H15NO5
• Molecular Weight: 229.233
• Hs Code.: 2933990090
• Mol file: 364077-84-9.mol

Synonyms:Boc-4-keto-D-proline;N-Boc-4-oxo-D-proline;4-Oxo-L-proline,N-BOC protected;

Chemical Property of (R)-4-OXO-PYRROLIDINE-1,2-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 42-46℃
• Boiling Point: 333.149°C at 760 mmHg
• Flash Point: 155.283°C
• PSA: 83.91000
• Density: 1.21g/cm³
• LogP: 0.58740
• Storage Temp.: Sealed in dry,Room Temperature

Purity/Quality:

99%, ^*data from raw suppliers

(2R)-N-Boc-4-oxo-proline ^*data from reagent suppliers

Safty Information:

• Pictogram(s): R20/21/22:; R41:
• Hazard Codes: Xn:Harmful
• Statements: R20/21/22:; R41:
• Safety Statements: S26:; S36/37:; S39:

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (2R)-N-Boc-4-oxo-proline was used as a reactant in the preparation of 4,4-disubstituted pyrrolidine-1,2-dicarboxamides which are potent factor Xa inhibitors with increased human half life. Also used in the synthesis of azacyclic FTY720 analogues which show potential for use in strategy to kill cancer cells as they restrict access to extracellular nutrients.

Technology Process of (R)-4-OXO-PYRROLIDINE-1,2-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER

There total 3 articles about (R)-4-OXO-PYRROLIDINE-1,2-DICARBOXYLIC ACID 1-TERT-BUTYL 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: 97.0%

(4R)-1-(tert-butoxycarbonyl)-4-hydroxy-D-proline (135042-12-5,946610-68-0) → (R)-1-(tert-butoxycarbonyl)-4-oxopyrrolidine-2-carboxylic acid (364077-84-9)

Guidance literature:

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; trichloroisocyanuric acid; In dichloromethane; at 0 - 20 ℃; for 3h;

DOI:10.1016/j.bmc.2009.01.063

Reference yield:

cis-hydroxy-D-proline (2584-71-6,30724-02-8) → (R)-1-(tert-butoxycarbonyl)-4-oxopyrrolidine-2-carboxylic acid (364077-84-9)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydroxide / tetrahydrofuran; water / 32 h / 20 °C

2: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; trichloroisocyanuric acid / dichloromethane / 0 - 20 °C

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; trichloroisocyanuric acid; sodium hydroxide; In tetrahydrofuran; dichloromethane; water;

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → (R)-1-(tert-butoxycarbonyl)-4-oxopyrrolidine-2-carboxylic acid (364077-84-9)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydroxide / tetrahydrofuran; water / 32 h / 20 °C

2: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; trichloroisocyanuric acid / dichloromethane / 0 - 20 °C

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; trichloroisocyanuric acid; sodium hydroxide; In tetrahydrofuran; dichloromethane; water;

upstream raw materials:

(4R)-1-(tert-butoxycarbonyl)-4-hydroxy-D-proline

cis-hydroxy-D-proline

di-tert-butyl dicarbonate

Downstream raw materials:

(R)-4-oxo-2-[4-(2-oxo-2H-pyridin-1-yl)-phenylcarbamoyl]-pyrrolidine-1-carboxylic acid tert-butyl ester

C₁₆H₂₀ClNO₅

C₁₇H₂₃NO₅

(2R,4S)-1-(tert-butoxycarbonyl)-4-(2,4-difluorophenyl)-4-hydroxypyrrolidine-2-carboxylic acid

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