Boc-D-Pro-Ome

Base Information

• Chemical Name: Boc-D-Pro-Ome
• CAS No.: 73323-65-6
• Molecular Formula: C11H19NO4
• Molecular Weight: 229.276
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID40361581
• Nikkaji Number: J1.629.084J
• Wikidata: Q72450548
• Mol file: 73323-65-6.mol

Synonyms:Boc-D-Pro-Ome;73323-65-6;boc-d-proline methyl ester;(R)-1-tert-Butyl 2-methyl pyrrolidine-1,2-dicarboxylate;N-Boc-D-proline methyl ester;1-TERT-BUTYL 2-METHYL (2R)-PYRROLIDINE-1,2-DICARBOXYLATE;1-O-tert-butyl 2-O-methyl (2R)-pyrrolidine-1,2-dicarboxylate;N-(tert-Butoxycarbonyl)-D-proline Methyl Ester;MFCD00190828;R-1-BOC-Pyrrolidine-2-carboxylic acid Methyl Ester;1-(tert-butyl) 2-methyl (R)-pyrrolidine-1,2-dicarboxylate;BOC-(R)-proline methyl ester;SCHEMBL1486184;DTXSID40361581;AKOS005258752;AC-2245;CS-W019985;DE-0044;AM20100703;B4787;A26496;EN300-196436;Q-101837;Methyl (R)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylate

Chemical Property of Boc-D-Pro-Ome

Chemical Property:

• Vapor Pressure: 0.00232mmHg at 25°C
• Refractive Index: 1.476
• Boiling Point: 288.6 °C at 760 mmHg
• PKA: -3.35±0.40(Predicted)
• Flash Point: 128.3 °C
• PSA: 55.84000
• Density: 1.12 g/cm³
• LogP: 1.49680
• Storage Temp.: Store at 0-5°C
• Solubility.: Soluble in DMSO.
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 229.13140809
• Heavy Atom Count: 16
• Complexity: 282

Purity/Quality:

99% ^*data from raw suppliers

Boc-D-proline methyl ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1CCCC1C(=O)OC
• Isomeric SMILES: CC(C)(C)OC(=O)N1CCC[C@@H]1C(=O)OC
• Uses: N-Boc-D-proline methyl ester is an important raw material and intermediate used in organic Synthesis, pharmaceuticals, agrochemicals and dyestuff fields.

Technology Process of Boc-D-Pro-Ome

There total 3 articles about Boc-D-Pro-Ome 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: 50.0%

(+/-)-N-tert-butoxycarbonylproline methyl ester (145681-01-2) → 1-(tert-butoxycarbonyl)-L-proline (15761-39-4,59433-50-0) + 1-(tert-butyl) 2-methyl (R)-pyrrolidine-1,2-dicarboxylate (73323-65-6)

Guidance literature:

With Candida antarctica lipase; In phosphate buffer; at 30 ℃; for 25h; pH=6.8;

DOI:10.1016/S0957-4166(03)00210-6

Reference yield:

methyl 1-(tert-butyloxycarbonyl)pyrrole-2-carboxylate (294659-30-6) → (S)-N-(tert-butoxycarbonyl)proline methyl ester (59936-29-7) + 1-(tert-butyl) 2-methyl (R)-pyrrolidine-1,2-dicarboxylate (73323-65-6)

Guidance literature:

With hydrogen; triethylamine; (S,S)-(R,R)-PhTRAP; In isopropyl alcohol; at 80 ℃; for 24h; under 38002.6 Torr; Title compound not separated from byproducts.;

DOI:10.1021/ja7102422

Reference yield:

4,5-dihydropyrrole-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester → (S)-N-(tert-butoxycarbonyl)proline methyl ester (59936-29-7) + 1-(tert-butyl) 2-methyl (R)-pyrrolidine-1,2-dicarboxylate (73323-65-6)

Guidance literature:

With [bis(2-methylallyl)cycloocta-1,5-diene]ruthenium(II); hydrogen; triethylamine; In isopropyl alcohol; at 60 ℃; for 24h; under 37503.8 Torr; Overall yield = 92 %; enantioselective reaction;

DOI:10.1080/10426507.2014.974752

upstream raw materials:

(+/-)-N-tert-butoxycarbonylproline methyl ester

methyl 1-(tert-butyloxycarbonyl)pyrrole-2-carboxylate

Downstream raw materials:

1-(tert-butoxycarbonyl)prolin-2R-ol

C₃₀H₂₈ClFN₄O₃S

(R)-N-(3-chloro-4-((3-fluorobenzyl)oxy)phenyl)-6-(pyrrolidin-2-ylethynyl)thieno[3,2-d]pyrimidin-4-amine

(R)-N-(tert-butoxycarbonyl)-2-(2-chloroacetyl)pyrrolidine

Refernces

• 1、 Kuwano, Ryoichi,Kashiwabara, Manabu,Ohsumi, Masato,Kusano, Hiroki. "Catalytic asymmetric hydrogenation of 2,3,5-trisubstituted pyrroles". . p. 808 - 809. Retrieved 2008/09/20.