tert-Butyl 5-oxo-L-prolinate

Base Information

• Chemical Name: tert-Butyl 5-oxo-L-prolinate
• CAS No.: 35418-16-7
• Molecular Formula: C₉H₁₅NO₃
• Molecular Weight: 185.223
• Hs Code.: 29339900
• European Community (EC) Number: 252-555-5,285-735-7
• DSSTox Substance ID: DTXSID20188899
• Nikkaji Number: J260.612G
• Wikidata: Q72505016
• Mol file: 35418-16-7.mol

Synonyms:35418-16-7;(S)-2-pyrrolidone-5-carboxylic acid t-butyl ester;tert-Butyl 5-oxo-L-prolinate;(S)-tert-Butyl 5-oxopyrrolidine-2-carboxylate;L-Pyroglutamic acid tert-butyl ester;tert-butyl (2S)-5-oxopyrrolidine-2-carboxylate;tert-Butyl L-Pyroglutamate;tert-Butyl (S)-2-pyrrolidone-5-carboxylate;Proline, 5-oxo-, 1,1-dimethylethyl ester;tert-Butyl (S)-5-Oxopyrrolidine-2-carboxylate;(S)-2-Pyrrolidone-5-carboxylicacidtert-butylester;EINECS 252-555-5;TERT-BUTYL (S)-5-OXO-2-PYRROLIDINECARBOXYLATE;(S)-5-Oxopyrrolidine-2-carboxylic Acid tert-Butyl Ester;tert-Butyl 5-oxo-DL-prolinate;EINECS 285-735-7;MFCD06659481;L-Pyroglutamicacidtert-butylester;H-Pyr-OtBu;(S)-5-Oxo-pyrrolidine-2-carboxylic acid tert-butyl ester;(R)-5-Oxo-pyrrolidine-2-carboxylic acid tert-butyl ester;(S)-tert-Butyl pyroglutamate;SCHEMBL716389;DTXSID20188899;QXGSPAGZWRTTOT-LURJTMIESA-N;5-Oxo-L-proline tert-butyl ester;1,1-dimethylethyl 5-oxo-L-prolinate;(2S)-5-oxo-proline tert-butyl ester;AKOS006294854;AKOS015838009;CS-W003321;GS-6801;HY-W003321;AC-23798;AM20090559;B4026;EN300-200160;A841230;A847242;J-502244;J-502433;(S)-pyrrolidin-2-one-5-carboxylic acid t-butyl ester;(2S)-5-Oxopyrrolidine-2-carboxylic acid tert-butyl ester;tert-Butyl (S)-2-pyrrolidone-5-carboxylate, >=98% (GC);(S)-2-PYRROLIDONE-5-CARBOXYLIC ACID TERT-BUTYL ESTER;5-Oxopyrrolidine-2a-carboxylic acid tert-butyl ester;Pyroglutamic acid tert-butyl ester;5-Oxopyrrolidine-2alpha-carboxylic acid tert-butyl ester

Chemical Property of tert-Butyl 5-oxo-L-prolinate

Chemical Property:

• Vapor Pressure: 0.000344mmHg at 25°C
• Melting Point: 102.0 to 108.0 °C
• Refractive Index: 1.467
• Boiling Point: 319.2 °C at 760 mmHg
• PKA: 14.65±0.40(Predicted)
• Flash Point: 146.8 °C
• PSA: 55.40000
• Density: 1.099 g/cm³
• LogP: 0.93550
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: soluble in Methanol
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 185.10519334
• Heavy Atom Count: 13
• Complexity: 230

Purity/Quality:

99% ^*data from raw suppliers

tert-Butyl5-oxo-L-prolinate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/38
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)C1CCC(=O)N1
• Isomeric SMILES: CC(C)(C)OC(=O)[C@@H]1CCC(=O)N1
• Uses: tert-Butyl (S)-2-pyrrolidone-5-carboxylate can be used:As a starting material/synthon in the synthesis of angiotensin-converting enzyme inhibitors.In the synthesis of phenanthroindolizidine alkaloids named (+)-tylophorine and antofine.As a starting material in the synthesis of radioligands [18F]IUR-1602 and [18F]IUR-1601, applicable for imaging of P2X7R, a therapeutic target for neuroinflammation.

Technology Process of tert-Butyl 5-oxo-L-prolinate

There total 17 articles about tert-Butyl 5-oxo-L-prolinate 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%

acetic acid tert-butyl ester (540-88-5) + L-Pyroglutamic acid (98-79-3) → L-t-butyl pyroglutamate (35418-16-7,85136-12-5)

Guidance literature:

With perchloric acid; In water; at 20 ℃; for 18h;

DOI:10.1081/SCC-200054223

Reference yield: 100.0%

t-butyl (4S)-t-6-[(5'S)-5'-(tert-butyloxycarbonyl)-2'-oxo-pyrrolidin-1'-yl]-r-4,c-5-dihydroxy-1,2-oxazinane-2-carboxylate (529483-99-6) → L-t-butyl pyroglutamate (35418-16-7,85136-12-5) + 1-[(t-butyloxycarbonyl)amino]-1-deoxy-D-erythritol

Guidance literature:

With hydrogen; nickel; In methanol; at 20 ℃; for 20h;

DOI:10.1016/S0040-4020(02)01512-0

Reference yield: 100.0%

tert-butyl (S)-N-tert-butoxycarbonylpyroglutamate (91229-91-3) → L-t-butyl pyroglutamate (35418-16-7,85136-12-5)

Guidance literature:

With ytterbium(III) triflate; In tetrahydrofuran; at 20 ℃; for 18h;

DOI:10.1021/jo050518r

upstream raw materials:

acetic acid tert-butyl ester

L-Pyroglutamic acid

isobutene

(S)-5-oxopyrrolidine-2-carbonyl chloride

Downstream raw materials:

N-(N-carbobenzyloxyglycyl)-L-pyroglutamic acid tert-butyl ester

N-(N-carbobenzyloxy-L-alanyl)-L-pyroglutamic acid tert-butyl ester

tert-butyl N-benzyloxycarbonyl-L-pyroglutamate

(S)-tert-butyl 1-benzyl-5-oxopyrrolidine-2-carboxylate

Refernces

• 1、 Calimsiz, Selcuk,Lipton, Mark A.. "Synthesis of N-Fmoc-(2S,3S,4R)-3,4-dimethylglutamine: An application of lanthanide-catalyzed transamidation". . p. 6218 - 6221. Retrieved 2005.
• 2、 Hossain, Md Imran,Thomas, Ajit G.,Mahdi, Fakhri,Adam, Amna T.,Akins, Nicholas S.,Woodard, Morgan M.,Paris, Jason J.,Slusher, Barbara S.,Le, Hoang V.. "An efficient synthetic route tol-γ-methyleneglutamine and its amide derivatives, and their selective anticancer activity". . p. 7115 - 7128. Retrieved 2021/02/26.
• 3、 Kazmierski, Wieslaw M.,Miriyala, Nagaraju,Johnson, David K.,Baskaran, Sam. "The Discovery of Conformationally Constrained Bicyclic Peptidomimetics as Potent Hepatitis C NS5A Inhibitors". supporting information. p. 1649 - 1655. Retrieved 2021/10/04.