N-Carbomethoxy proline

Base Information

• Chemical Name: N-Carbomethoxy proline
• CAS No.: 74761-41-4
• Molecular Formula: C7H11 N O4
• Molecular Weight: 173.169
• Hs Code.: 2933990090
• UNII: SFB41ANL16
• Nikkaji Number: J1.151.475H
• Wikidata: Q27289179
• Mol file: 74761-41-4.mol

Synonyms:74761-41-4;N-Carbomethoxy proline;1-(methoxycarbonyl)-L-proline;(S)-1-(methoxycarbonyl)pyrrolidine-2-carboxylic acid;N-Methoxycarbonyl-L-proline;N-Carbomethoxy proline, L-;SFB41ANL16;(2S)-1-methoxycarbonylpyrrolidine-2-carboxylic acid;1,2-Pyrrolidinedicarboxylic acid, 1-methyl ester, (2S)-;(2S)-1-(methoxycarbonyl)pyrrolidine-2-carboxylic acid;UNII-SFB41ANL16;SCHEMBL9169924;N-CARBOMETHOXY-L-PROLINE;PNXXTNFAEIJNDV-YFKPBYRVSA-N;MFCD12795354;AKOS010373855;LS-07028;CS-0069007;D73661;(S)-1-(methoxycarbonyl)pyrrolidine-2-carboxylicacid;Q27289179

Chemical Property of N-Carbomethoxy proline

Chemical Property:

• Boiling Point: 317.2±35.0 °C(Predicted)
• PKA: 4.00±0.20(Predicted)
• PSA: 66.84000
• Density: 1.335±0.06 g/cm3(Predicted)
• LogP: 0.23970
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 173.06880783
• Heavy Atom Count: 12
• Complexity: 204

Purity/Quality:

98.5% ^*data from raw suppliers

1-(Methoxycarbonyl)-L-proline ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)N1CCCC1C(=O)O
• Isomeric SMILES: COC(=O)N1CCC[C@H]1C(=O)O

Technology Process of N-Carbomethoxy proline

There total 2 articles about N-Carbomethoxy 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: 89.0%

methyl chloroformate (79-22-1) + L-proline (147-85-3,25191-13-3,37159-97-0,4305-67-3,4607-28-7) → (S)-1-(methoxycarbonyl)pyrrolidine-2-carboxylic acid (74761-41-4,134250-76-3)

Guidance literature:

With sodium hydrogencarbonate; In tetrahydrofuran; at 20 ℃;

DOI:10.1021/jo000356t

Reference yield:

methyl chloroformate (79-22-1) → (S)-1-(methoxycarbonyl)pyrrolidine-2-carboxylic acid (74761-41-4,134250-76-3)

Guidance literature:

With sodium hydroxide; sodium carbonate;

Reference yield: 91.0%

(S)-1-((R)-4-Benzyl-4,5-dihydro-oxazol-2-yl)-2-methyl-propylamine (852049-32-2) + (S)-1-(methoxycarbonyl)pyrrolidine-2-carboxylic acid (74761-41-4,134250-76-3) → (S)-methyl 2-((S)-1-((R)-4-benzyl-4,5-dihydrooxazol-2-yl)-2-methylpropylcarbamoyl)pyrrolidine-1-carboxylate (1008530-27-5)

Guidance literature:

(S)-1-(methoxycarbonyl)pyrrolidine-2-carboxylic acid; With 4-methyl-morpholine; isobutyl chloroformate; In dichloromethane; at -5 ℃; for 0.75h;

(S)-1-((R)-4-Benzyl-4,5-dihydro-oxazol-2-yl)-2-methyl-propylamine; In dichloromethane; at -5 - 20 ℃; for 3h; Further stages.;

DOI:10.1002/anie.200704257

upstream raw materials:

methyl chloroformate

L-proline

Downstream raw materials:

(S)-proline-N-carboxyanhydride

(S)-dimethyl pyrrolidine-1,2-dicarboxylate

methyl 2-hydroxy-1-pyrrolidinecarboxylate

methyl 2-methoxypyrrolidine-1-carboxylate

Refernces

• 1、 -. "THERAPEUTICALLY ACTIVE COMPOUNDS AND THEIR METHODS OF USE". Page/Page column. . Retrieved 2015/03/31.
• 2、 Boto, Alicia,Hernandez, Rosendo,Suarez, Ernesto. "Tandem radical decarboxylation-oxidation of amino acids: A mild and efficient method for the generation of N-acyliminium ions and their nucleophilic trapping". . p. 4930 - 4937. Retrieved 2007/10/03.