(S)-Methyl 2-((tert-butoxycarbonyl)amino)-3-methylbutanoate

Base Information

• Chemical Name: (S)-Methyl 2-((tert-butoxycarbonyl)amino)-3-methylbutanoate
• CAS No.: 58561-04-9
• Molecular Formula: C11H21NO4
• Molecular Weight: 231.292
• DSSTox Substance ID: DTXSID60452647
• Nikkaji Number: J594.751K
• Wikidata: Q72510545
• Mol file: 58561-04-9.mol

Synonyms:58561-04-9;Boc-Val-OMe;(S)-Methyl 2-((tert-butoxycarbonyl)amino)-3-methylbutanoate;Boc-L-valine methyl ester;N-(tert-Butoxycarbonyl)-L-valine methyl ester;methyl (2S)-3-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoate;N-Boc-L-valine Methyl Ester;(S)-methyl 2-(tert-butoxycarbonylamino)-3-methylbutanoate;L-Valine, N-[(1,1-dimethylethoxy)carbonyl]-, methyl ester;Boc-L-valine methylester;SCHEMBL1505521;DTXSID60452647;XCJLIYKAMLUDGN-QMMMGPOBSA-N;(S)-METHYL 2-(TERT-BUTOXYCARBONYL AMINO)-3-METHYLBUTANOATE;MFCD00672510;AKOS008227297;AM82376;CS-W008593;N-t-butoxycarbonyl-L-valine methyl ester;DS-15180;HY-41048;PD195991;N-(tert-Butoxycarbonyl)valine methyl ester;B6020;N-(tert-Butoxycarbonyl)-(L)-valine methyl ester;N-(tert.-butyloxycarbonyl)-L-valine methyl ester;A869412;J-300296;N-(tert-Butoxycarbonyl)-L-valine methyl ester, 98%;(S)-Methyl2-((tert-butoxycarbonyl)amino)-3-methylbutanoate;(S)-Methyl 2-((tert-butoxycarbonyl)amino)-3-methylbutanoate (Boc-L-Val-OMe)

Chemical Property of (S)-Methyl 2-((tert-butoxycarbonyl)amino)-3-methylbutanoate

Chemical Property:

• Vapor Pressure: 0.001mmHg at 25°C
• Melting Point: 194℃
• Refractive Index: n20/D 1.44(lit.)
• Boiling Point: 306.042 °C at 760 mmHg
• PKA: 11.13±0.46(Predicted)
• Flash Point: 138.889 °C
• PSA: 64.63000
• Density: 1.02 g/cm³
• LogP: 2.09960
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 231.14705815
• Heavy Atom Count: 16
• Complexity: 255

Purity/Quality:

99% ^*data from raw suppliers

Boc-L-Val-OMe ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C(C(=O)OC)NC(=O)OC(C)(C)C
• Isomeric SMILES: CC(C)[C@@H](C(=O)OC)NC(=O)OC(C)(C)C
• Uses: Boc-L-Val-OMe is an intermediate used in the asymmetric synthesis of isoxazoline and hydroxyketomethylene dipeptide isosteres via dipolar nitrile oxide cycloaddition. It is also used to prepare nonsymmetric dihydroxyethylene dipeptide isosteres via epoxyalcohols derived from α-amino acids.

Technology Process of (S)-Methyl 2-((tert-butoxycarbonyl)amino)-3-methylbutanoate

There total 11 articles about (S)-Methyl 2-((tert-butoxycarbonyl)amino)-3-methylbutanoate 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: 97.0%

di-tert-butyl dicarbonate (24424-99-5) + N-(Benzyloxycarbonyl)valine methyl ester (134306-34-6) → N-Boc-valine methyl ester (58561-04-9,106391-85-9,145618-65-1)

Guidance literature:

With triethylsilane; palladium diacetate; triethylamine; In ethanol; for 15h; Ambient temperature;

DOI:10.1016/0040-4039(88)85064-0

Reference yield: 86.0%

di-tert-butyl dicarbonate (24424-99-5) + DL-valine methyl ester hydrochloride (5619-05-6,6306-52-1,7146-15-8) → N-Boc-valine methyl ester (58561-04-9,106391-85-9,145618-65-1)

Guidance literature:

With 4-methyl-morpholine; In dichloromethane; at 20 ℃; for 12h;

DOI:10.1016/j.tetasy.2011.07.019

Reference yield: 79.1%

N-Boc-(S/R)-valine (13734-41-3,22838-58-0,54895-12-4) + methyl iodide (74-88-4) → N-Boc-valine methyl ester (58561-04-9,106391-85-9,145618-65-1)

Guidance literature:

With ammonium bicarbonate; In N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1007/s10562-017-1999-3

upstream raw materials:

di-tert-butyl dicarbonate

N-(Benzyloxycarbonyl)valine methyl ester

methanol

N-Boc-(S/R)-valine

Downstream raw materials:

Boc-Val-CH2Cl

(3S,R(S))-N-(tert-butoxycarbonyl)-3-amino-4-methyl-1-(p-tolylsulfinyl)-2-pentanone

C₂₂H₃₅NO₄Si

(S)-4-i-propyl-5,5-dimethyl-3-[(RP)-methyl(phenyl)phosphinoyll]oxazolidin-2-one

Refernces

• 1、 Malavasic, Crt,Stanovnik, Branko,Wagger, Jernej,Svete, Jurij. "The effect of substituents on the chiral solvating properties of (S)-1,6-dialkylpiperazine-2,5-diones". experimental part. p. 1364 - 1371. Retrieved 2011/11/29.
• 2、 Sameiro,Goncalves,Maia, Hernani L.S.. "Development of a temporary marker for peptides". . p. 1480 - 1485. Retrieved 2007/10/03.