N-Boc-cis-4-hydroxy-L-proline methyl ester

Base Information

• Chemical Name: N-Boc-cis-4-hydroxy-L-proline methyl ester
• CAS No.: 102195-79-9
• Molecular Formula: C₁₁H₁₉NO₅
• Molecular Weight: 245.276
• Hs Code.: 29339900
• European Community (EC) Number: 627-146-3
• DSSTox Substance ID: DTXSID50444435
• Nikkaji Number: J1.509.014F
• Wikidata: Q72449635
• Mol file: 102195-79-9.mol

Synonyms:102195-79-9;N-Boc-cis-4-hydroxy-L-proline methyl ester;Boc-cis-Hyp-Ome;(2S,4S)-1-tert-butyl 2-methyl 4-hydroxypyrrolidine-1,2-dicarboxylate;1-tert-Butyl 2-Methyl (2S,4S)-4-Hydroxypyrrolidine-1,2-dicarboxylate;(2S,4S)-4-Hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester;MFCD00237541;Boc-cis-4-Hydroxy-L-proline methyl ester;1-O-tert-butyl 2-O-methyl (2S,4S)-4-hydroxypyrrolidine-1,2-dicarboxylate;227935-38-8;O1-TERT-BUTYL O2-METHYL (2S,4S)-4-HYDROXYPYRROLIDINE-1,2-DICARBOXYLATE;1,2-PYRROLIDINEDICARBOXYLIC ACID, 4-HYDROXY-, 1-(1,1-DIMETHYLETHYL) 2-METHYL ESTER, (2S,4S)-;Boc-trans-4-Hydroxy-L-proline methyl ester;cis-Boc-Hyp-OMe;N-Boc-cis-4-Hydroxy-L-prolinemethylester;BOC-CIS-L-4-HYDROXYPROLINE METHYL ESTER;SCHEMBL85695;DTXSID50444435;MZMNEDXVUJLQAF-YUMQZZPRSA-N;CS-D1415;HY-Y0755;1-(tert-butyl) 2-methyl (2S,4S)-4-hydroxypyrrolidine-1,2-dicarboxylate;AKOS015850982;AKOS015917747;(2S,4S)-4-Hydroxypyrrolidine-1,2-dicarboxylic Acid 1-tert-Butyl 2-Methyl Ester;N-Boc-cis-4-hydroxyproline methyl ester;AM808131;AS-11200;N-Boc-cis-4-hydroxy proline methyl ester;N-Boc-cis-4-hydroxy-L-proline methylester;B3987;EN300-187965;METHYL CIS-1-BOC-4-HYDROXY-L-PROLINATE;P15767;N-Boc-cis-4-hydroxy-L-proline methyl ester, 97%;(2S,4S)-methyl N-Boc-4-hydroxypyrrolidine-2-carboxylate;N-tert-butoxycarbonyl-cis-4-hydroxy-L-proline methyl ester;(2S,4S)-2-methyl N-Boc-4-hydroxy-pyrrolidine-2-carboxylate;1-(tert-Butoxycarbonyl)-4alpha-hydroxy-L-proline methyl ester;cis-1-tert-Butyl2-methyl4-hydroxypyrrolidine-1,2-dicarboxylate;N-(tert-butoxycarbonyl)-(2S,4S)-4-hydroxyproline methyl ester;N-(tert-Butoxycarbonyl)-cis-4-hydroxy-L-proline Methyl Ester;(2S,4S)-1-t-butoxycarbonyl-4-hydroxy-2- methoxycarbonylpyrrolidine;(2S,4S)-1-t-butoxycarbonyl-4-hydroxy-2-methoxycarbonylpyrrolidine;1-t-butyl 2-methyl (2S,4S)-4-hydroxypyrrolidine-1,2-dicarboxylate;1-t-butyl 2-methyl(2s,4s)-4-hydroxypyrrolidine-1,2-dicarboxylate;1-tert-butyl 2-methyl (2S,4S)-4-hydroxypyrrolidine-1,2-dioate;cis-1-tert-Butyl 2-methyl 4-hydroxypyrrolidine-1,2-dicarboxylate;1-tert-Butyl 2-Methyl (2S,4S)-4-hydroxypyrrolidine -1,2-dicarboxylate;1-tert-butyl 2-methyl(2s,4s)-4-hydroxypyrrolidine-1,2-dicarboxylate;methyl (2S,4S)-1-tert-butoxycarbonyl-4-hydroxy-2-pyrrolidinylcarboxylate;(2S, 4S)-4-Hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyester;(2S, 4S)-4-Hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester;(2S,4S)-4-Hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyester

Chemical Property of N-Boc-cis-4-hydroxy-L-proline methyl ester

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 82-86 °C(lit.)
• 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: 1.216 g/cm³
• LogP: 0.46760
• Storage Temp.: -15°C
• Water Solubility.: Insoluble in water.
• 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:

98%, ^*data from raw suppliers

N-Boc-cis-4-hydroxy-L-proline methyl ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-36/37/38-43
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

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: Used as a local anaesthetic. Used as therapeutic agents. Employed as important intermediates in various areas such as peptide synthesis, polymer chemistry.. 2S,4S)-4-Hydroxypyrrolidine-1,2-dicarboxylic Acid 1-tert-Butyl Ester 2-Methyl Ester oline scaffold.

Technology Process of N-Boc-cis-4-hydroxy-L-proline methyl ester

There total 31 articles about N-Boc-cis-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:

(2S,4S)-1-t-butoxycarbonyl-4-formyloxy-2-methoxycarbonylpyrrolidine

Boc-(2S,4S)-p-nitrobenzoate-4-hydroxyproline methyl ester

di-tert-butyl dicarbonate

cis-L-hydroxyproline methyl ester

Downstream raw materials:

(2S,4R)-4-(3-Benzoyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

N-Boc-L-trans-Pro(4-<4-<(E)-2-(4-cyanophenyl)-1-diazenyl>phenoxy>)-OMe

O2-methyl O1-tert-butyl (2S,4S)-4-(p-tolylsulfonyloxy)pyrrolidine-1,2-dicarboxylic acid

1-tert-butyl 2-methyl (2S,4S)-4-{[(4-bromo-phenyl)sulfonyl]oxy}-pyrrolidine-1,2-dicarboxylate

Refernces

• 1、 Forbes, Christina R.,Pandey, Anil K.,Ganguly, Himal K.,Yap, Glenn P. A.,Zondlo, Neal J.. "4R- and 4S-iodophenyl hydroxyproline, 4R-pentynoyl hydroxyproline, and S-propargyl-4-thiolphenylalanine: Conformationally biased and tunable amino acids for bioorthogonal reactions". . p. 2327 - 2346. Retrieved 2016.
• 2、 Seo, Jiwon,Martasek, Pavel,Roman, Linda J.,Silverman, Richard B.. "Selective l-nitroargininylaminopyrrolidine and l-nitroargininylaminopiperidine neuronal nitric oxide synthase inhibitors". . p. 1928 - 1938. Retrieved 2007.
• 3、 Hajduch, Jan,Fabre, Benjamin,Klopp, Benjamin,Pohl, Radek,Budě?ínsky, Milo?,?olínová, Veronika,Ka?i?ka, Václav,K?prülüoglu, Cemal,Eyrilmez, Saltuk Mustafa,Lep?ík, Martin,Hobza, Pavel,Mitrová, Katarína,Lubos, Marta,Hernández, María Soledad Garre,Jirá?ek, Ji?í. "Multipodal insulin mimetics built on adamantane or proline scaffolds". . . Retrieved 2021.
• 4、 Gomez-Vidal, Jose A.,Silverman, Richard B.. "Short, highly efficient syntheses of protected 3-azido- and 4-azidoproline and their precursors". . p. 2481 - 2484. Retrieved 2001.
• 5、 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.