(R)-2-((tert-Butoxycarbonyl)(methyl)amino)-3-methylbutanoic acid

Base Information

• Chemical Name: (R)-2-((tert-Butoxycarbonyl)(methyl)amino)-3-methylbutanoic acid
• CAS No.: 89536-85-6
• Molecular Formula: C₁₁H₂₁NO₄
• Molecular Weight: 231.292
• Hs Code.: 2924299090
• DSSTox Substance ID: DTXSID20427033
• Nikkaji Number: J2.214.924E
• Wikidata: Q72510318
• Mol file: 89536-85-6.mol

Synonyms:89536-85-6;(R)-2-((tert-Butoxycarbonyl)(methyl)amino)-3-methylbutanoic acid;Boc-N-methyl-D-Valine;BOC-D-MEVAL-OH;Boc-D-N-Me-Val-OH;Boc-Nalpha-methyl-D-valine;N-(tert-butoxycarbonyl)-N-methyl-D-valine;Boc-N-Alpha-Methyl-D-valine;(2R)-3-methyl-2-[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]butanoic acid;(R)-2-(tert-butoxycarbonyl(methyl)amino)-3-methylbutanoic acid;Boc-N-Me-D-Val-OH;SCHEMBL2160514;DTXSID20427033;XPUAXAVJMJDPDH-MRVPVSSYSA-N;MFCD00076996;AKOS015836737;AM82397;HY-W022593;AC-19306;AS-19325;PD197068;CS-0041825;F11530;A850901;N-alpha-t-Butyloxycarbonyl-N-alpha-methyl-D-valine;(R)-2-((tert-Butoxycarbonyl)(methyl)amino)-3-methylbutanoic acid Boc-N-Me-D-Val-OH

Chemical Property of (R)-2-((tert-Butoxycarbonyl)(methyl)amino)-3-methylbutanoic acid

Chemical Property:

• Boiling Point: 322.4 °C at 760 mmHg
• PKA: 4.03±0.10(Predicted)
• Flash Point: 148.8 °C
• PSA: 66.84000
• Density: 1.069 g/cm³
• LogP: 1.96250
• Storage Temp.: Store at 0-5°C
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 231.14705815
• Heavy Atom Count: 16
• Complexity: 268

Purity/Quality:

98%min ^*data from raw suppliers

Boc-N-methyl-D-valine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C(C(=O)O)N(C)C(=O)OC(C)(C)C
• Isomeric SMILES: CC(C)[C@H](C(=O)O)N(C)C(=O)OC(C)(C)C

Technology Process of (R)-2-((tert-Butoxycarbonyl)(methyl)amino)-3-methylbutanoic acid

There total 3 articles about (R)-2-((tert-Butoxycarbonyl)(methyl)amino)-3-methylbutanoic acid 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%

Boc-D-Val-OH (22838-58-0) + methyl iodide (74-88-4) → (R)-2-(tert-butoxycarbonyl(methyl)amino)-3-methylbutanoic acid (13850-91-4,45170-31-8,89536-85-6)

Guidance literature:

Boc-D-Val-OH; With sodium hydride; In tetrahydrofuran; mineral oil; at 0 ℃; for 0.5h; Inert atmosphere;

methyl iodide; In tetrahydrofuran; mineral oil; at 20 ℃; for 36h; Inert atmosphere;

DOI:10.1039/c5ob02505b

Reference yield:

D-Val-OH (640-68-6,25609-85-2,7004-03-7,921-10-8) + di-tert-butyl dicarbonate (24424-99-5) + methyl iodide (74-88-4) → (R)-2-(tert-butoxycarbonyl(methyl)amino)-3-methylbutanoic acid (13850-91-4,45170-31-8,89536-85-6)

Guidance literature:

D-Val-OH; di-tert-butyl dicarbonate; With sodium hydroxide; In 1,4-dioxane;

methyl iodide; In tetrahydrofuran;

DOI:10.1021/ol0478786

Reference yield:

carbon dioxide (124-38-9,18923-20-1) + Methyl-((S)-2-methyl-1-tributylstannanyl-propyl)-carbamic acid tert-butyl ester (140175-19-5,140384-74-3) → (R)-2-(tert-butoxycarbonyl(methyl)amino)-3-methylbutanoic acid (13850-91-4,45170-31-8,89536-85-6)

Guidance literature:

With n-butyllithium; Yield given. Multistep reaction; 1.) THF, -95 deg C, 10 min, 2.) -95 deg C;

DOI:10.1021/jo00034a007

upstream raw materials:

carbon dioxide

Methyl-((S)-2-methyl-1-tributylstannanyl-propyl)-carbamic acid tert-butyl ester

Boc-D-Val-OH

methyl iodide

Downstream raw materials:

(R)-2-{(R)-2-[(R)-2-(tert-Butoxycarbonyl-methyl-amino)-3-methyl-butyrylamino]-4-methyl-pentanoylamino}-3-phenyl-propionic acid methyl ester

(R)-2-((R)-2-{[(R)-2-(tert-Butoxycarbonyl-methyl-amino)-3-methyl-butyryl]-methyl-amino}-4-methyl-pentanoylamino)-3-phenyl-propionic acid methyl ester

Refernces

• 1、 Casalme, Loida O.,Yamauchi, Arisa,Sato, Akinori,Petitbois, Julie G.,Nogata, Yasuyuki,Yoshimura, Erina,Okino, Tatsufumi,Umezawa, Taiki,Matsuda, Fuyuhiko. "Total synthesis and biological activity of dolastatin 16". supporting information. p. 1140 - 1150. Retrieved 2017/02/10.
• 2、 Li,Lu,Wu,Yu,Xu,Qiu,Pei,Lin,Pang. "Design, SAR, angiogenic activities evaluation and pro-angiogenic mechanism of new marine cyclopeptide analogs". . p. 1183 - 1194. Retrieved 2013/07/28.