N-Boc-trans-4-Hydroxy-L-proline methyl ester

Base Information

• Chemical Name: N-Boc-trans-4-Hydroxy-L-proline methyl ester
• CAS No.: 74844-91-0
• Molecular Formula: C11H19NO5
• Molecular Weight: 245.276
• Hs Code.: 29339900
• European Community (EC) Number: 616-143-2
• DSSTox Substance ID: DTXSID00370553
• Nikkaji Number: J836.003K
• Mol file: 74844-91-0.mol

Synonyms:1,2-Pyrrolidinedicarboxylicacid, 4-hydroxy-, 1-(1,1-dimethylethyl) 2-methyl ester, (2S-trans)-;(2S,4R)-1-tert-Butoxycarbonyl-4-hydroxypyrrolidine-2-carboxylic acid methylester;1-tert-Butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate;1-tert-Butyl 2-methyl 4(R)-hydroxypyrrolidine-1,2(S)-dicarboxylate;Methyl(2S,4R)-1-(tert-butoxycarbonyl)-4-hydroxypyrrolidine-2-carboxylate;Methyl(4R)-N-Boc-4-hydroxy-L-prolinate;N-(tert-Butoxycarbonyl)-(2S,4R)-4-hydroxyproline methyl ester;N-tert-Butoxycarbonyl-L-hydroxyprolinemethyl ester;tert-Butyl(2S,4R)-2-(methoxycarbonyl)-4-hydroxypyrrolidine-1-carboxylate;Boc-Hyp-OMe;

Chemical Property of N-Boc-trans-4-Hydroxy-L-proline methyl ester

Chemical Property:

• Appearance/Colour: Clear colourless oil
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 91-96 °C
• Refractive Index: 1.501
• Boiling Point: 335.244 °C at 760 mmHg
• PKA: 14.27±0.40(Predicted)
• Flash Point: 156.55 °C
• PSA: 76.07000
• Density: 1.217 g/cm³
• LogP: 0.46760
• Storage Temp.: 2-8°C
• Solubility.: Soluble in chloroform, dichloromethane and ethyl acetate.
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 245.12632271
• Heavy Atom Count: 17
• Complexity: 310

Purity/Quality:

Min 98% ^*data from raw suppliers

(2S,4R)-4-Hydroxypyrrolidine-1,2-dicarboxylicAcid1-tert-ButylEster2-MethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 24/25-36-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1CC(CC1C(=O)OC)O
• Isomeric SMILES: CC(C)(C)OC(=O)N1C[C@@H](C[C@H]1C(=O)OC)O
• Uses: A potential iNOS inhibitor. (2S,4R)-4-Hydroxypyrrolidine-1,2-dicarboxylic Acid 1-tert-Butyl Ester 2-Methyl Ester roline scaffold. It is used in the synthesis of For-Met-Leu-Phe-OMe (fMLF-OMe) analogues based on Met residue replacement by 4-amino-proline scaffold.

Technology Process of N-Boc-trans-4-Hydroxy-L-proline methyl ester

There total 65 articles about N-Boc-trans-4-Hydroxy-L-proline methyl 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: 100.0%

methanol (67-56-1) + 2’-methyl-2’-propanyl (1S,4S)-3-oxo-2-oxa-5-azabicyclo[2.2.1]heptane-5-carboxylate (87250-97-3,113775-22-7) → (2S,4S)-N-tert-butoxycarbonyl-4-hydroxyproline methyl ester (74844-91-0,114676-69-6,135042-17-0,227935-38-8,102195-79-9)

Guidance literature:

With sodium azide;

DOI:10.1021/ol0161054

Reference yield: 98.4%

1-tert-butyl 2-methyl (2S,4S)-4-((benzoyl)oxy)-1,2-pyrrolidinedicarboxylate (121147-94-2) → (2S,4S)-N-tert-butoxycarbonyl-4-hydroxyproline methyl ester (74844-91-0,114676-69-6,135042-17-0,227935-38-8,102195-79-9)

Guidance literature:

With potassium carbonate; In methanol; at 20 ℃; for 1h;

DOI:10.1016/S0968-0896(01)00397-2

Reference yield: 95.0%

Boc-(2S,4S)-p-nitrobenzoate-4-hydroxyproline methyl ester (168264-25-3) → (2S,4S)-N-tert-butoxycarbonyl-4-hydroxyproline methyl ester (74844-91-0,114676-69-6,135042-17-0,227935-38-8,102195-79-9)

Guidance literature:

With sodium methylate; In methanol;

DOI:10.1016/S0960-894X(97)00079-6

upstream raw materials:

diazomethane

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

di-tert-butyl dicarbonate

L-4-hydroxyproline methyl ester hydrochloride

Downstream raw materials:

1-(tert-butyl) 2-methyl (2S,4R)-4-(benzyloxy)pyrrolidine-1,2-dicarboxylate

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

(4R)-4-[(4'-bromobenzyl)oxy]-N-Boc-L-proline methyl ester

tert-butyl (2S,4R)-2-(aminocarbonyl)-4-hydroxypyrrolidine-1-carboxylate

Refernces

• 1、 Okamoto, Kazuhiro,Shoji, Takao,Tsutsui, Mizuki,Shida, Naoki,Chiba, Kazuhiro. "Synthesis of Ribo-Azanucleosides by Anodic Oxidation: Reactivity Control of Intermediate for Efficient Access to Pharmacophores". . p. 17902 - 17905. Retrieved 2018.
• 2、 Craig, William,Chen, Janet,Richardson, David,Thorpe, Rondel,Yuan, Yu. "A Highly Stereoselective and Scalable Synthesis of l -allo-Enduracididine". . p. 4620 - 4623. Retrieved 2015.
• 3、 Braun, Alexandra,Gallo, Francesca,Hambira, Chido M.,Hechler, Torsten,Kato, Brandon,Müller, Christoph,Matinkhoo, Kaveh,Pahl, Andreas,Perrin, David M.,Wei, Charlie,Wong, Antonio A. W. L.. "Design, Synthesis, and Biochemical Evaluation of Alpha-Amanitin Derivatives Containing Analogs of the trans-Hydroxyproline Residue for Potential Use in Antibody-Drug Conjugates". supporting information. p. 10282 - 10292. Retrieved 2021/06/25.
• 4、 Bonneure, Eli,De Baets, Amber,De Decker, Sam,Van den Berge, Koen,Clement, Lieven,Vyverman, Wim,Mangelinckx, Sven. "Altering the sex pheromone cyclo(L-pro-l-pro) of the diatom seminavis robusta towards a chemical probe". . p. 1 - 14. Retrieved 2021/01/26.