(S)-tert-Butyl 2-carbamoyl-2,3-dihydro-1H-pyrrole-1-carboxylate

Base Information

• Chemical Name: (S)-tert-Butyl 2-carbamoyl-2,3-dihydro-1H-pyrrole-1-carboxylate
• CAS No.: 709031-38-9
• Molecular Formula: C10H16N2O3
• Molecular Weight: 212.249
• Hs Code.: 2933990090
• European Community (EC) Number: 615-204-0
• DSSTox Substance ID: DTXSID80433776
• Nikkaji Number: J2.323.758J
• Wikidata: Q72434118
• Mol file: 709031-38-9.mol

Synonyms:709031-38-9;(S)-tert-Butyl 2-carbamoyl-2,3-dihydro-1H-pyrrole-1-carboxylate;Tert-butyl (2S)-2-carbamoyl-2,3-dihydropyrrole-1-carboxylate;tert-butyl (S)-2-carbamoyl-2,3-dihydro-1H-pyrrole-1-carboxylate;(s)-tert-butyl 2-carbamoyl-2,3-dihydropyrrole-1-carboxylate;tert-Butyl (2S)-2-carbamoyl-2,3-dihydro-1H-pyrrole-1-carboxylate;(S)-Boc-2-carbamoyl-2,3-dihydro-1H-pyrrole;1H-Pyrrole-1-carboxylic acid, 2-(aminocarbonyl)-2,3-dihydro-, 1,1-dimethylethyl ester, (2S)-;SCHEMBL3294057;DTXSID80433776;ZDKSDALJIXEHOP-ZETCQYMHSA-N;BCP06238;CS-0183500;1-(tert-Butoxycarbonyl)-4,5-didehydroprolinamide;A866524;(s)-t-butyl 2-carbamoyl-2,3-dihydro-1h-pyrrole-1-carboxylate;(S)-tert-Butyl2-carbamoyl-2,3-dihydro-1H-pyrrole-1-carboxylate

Chemical Property of (S)-tert-Butyl 2-carbamoyl-2,3-dihydro-1H-pyrrole-1-carboxylate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.523
• Boiling Point: 386.461 °C at 760 mmHg
• PKA: 15.57±0.20(Predicted)
• Flash Point: 187.525 °C
• PSA: 73.62000
• Density: 1.188 g/cm³
• LogP: 2.08240
• Storage Temp.: 2-8°C
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 212.11609238
• Heavy Atom Count: 15
• Complexity: 304

Purity/Quality:

98% ^*data from raw suppliers

(S)-Boc-2-carbamoyl-2,3-dihydro-1H-pyrrole ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1C=CCC1C(=O)N
• Isomeric SMILES: CC(C)(C)OC(=O)N1C=CC[C@H]1C(=O)N
• Uses: (S)-Boc-2-carbamoyl-2,3-dihydro-1H-pyrrole is an impurity of Saxagliptin (S143500), which is a potent and selective reversible inhibitor of dipeptidyl peptidase-4, which is being developed for the treatment of type 2 diabetes. It is absorbed rapidly after oral administration and has a pharmacokinetic profile compatible with once daily dosing.

Technology Process of (S)-tert-Butyl 2-carbamoyl-2,3-dihydro-1H-pyrrole-1-carboxylate

There total 18 articles about (S)-tert-Butyl 2-carbamoyl-2,3-dihydro-1H-pyrrole-1-carboxylate 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: 93.0%

(5S)-4,5-dihydro-1H-pyrrol-1,5-dicarboxylic acid [1-(1,1-dimethylethyl)] 5-ethyl ester (178172-26-4) → (5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester (709031-38-9)

Guidance literature:

With sodium isopropylate; formamide; In diethyl ether; at 20 ℃; for 2.16667h; Solvent; Temperature; Cooling with ice;

Reference yield: 90.0%

(S)-1-(tert-butoxycarbonyl)-2,3-dihydro-1H-pyrrole-2-carboxylic acid diisopropylethylamine salt (709031-37-8) → (5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester (709031-38-9)

Guidance literature:

(S)-1-(tert-butoxycarbonyl)-2,3-dihydro-1H-pyrrole-2-carboxylic acid diisopropylethylamine salt; With methanesulfonyl chloride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at -20 - 0 ℃; for 3h;

With ammonium carbonate; In tetrahydrofuran; at 0 - 20 ℃;

Reference yield: 90.0%

1-(tert-butoxycarbonyl)-2,3-dihydro-1H-pyrrole-2-carboxylic acid (90104-21-5) → (5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester (709031-38-9)

Guidance literature:

1-(tert-butoxycarbonyl)-2,3-dihydro-1H-pyrrole-2-carboxylic acid; With methanesulfonyl chloride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at -25 - -20 ℃; for 2h; Large scale;

With ammonia; In tetrahydrofuran; at 0 - 20 ℃; for 3h; Large scale;

upstream raw materials:

(5S)-4,5-dihydro-1H-pyrrol-1,5-dicarboxylic acid [1-(1,1-dimethylethyl)] 5-ethyl ester

4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride

di-tert-butyl dicarbonate

5-hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester

Downstream raw materials:

3-cyano-(αS)-α-(3-hydroxytricyclo[3.3.1.1^3,7]dec-1-yl)-β-oxo-(1S,3S,5S)-2-azabicyclo[3.1.0]hexane-2-ethanecarbamic acid 1,1-dimethylethyl ester

saxagliptin

(R)-3-hydroxyadamantylglycine-L-cis-4,5-methanoprolinenitrile

(1S,3S,5S)-2-azabicyclo[3.1.0]hexane-3-carboxamide methane sulphonic acid

Refernces

• 1、 -. "Preparation method of key intermediate of saxagliptin". Paragraph 0036; 0037. . Retrieved 2017/06/02.
• 2、 -. "PROCESS FOR PREPARING DIPEPTIDYL PEPTIDASE IV INHIBITORS AND INTERMEDIATES THEREFOR". . . Retrieved 2016/07/27.