BOC-N-methyl-D-alanine

Base Information

• Chemical Name: BOC-N-methyl-D-alanine
• CAS No.: 19914-38-6
• Molecular Formula: C₉H₁₇NO₄
• Molecular Weight: 203.238
• Hs Code.: 29241990
• European Community (EC) Number: 675-994-8
• DSSTox Substance ID: DTXSID60583400
• Wikidata: Q72449897
• Mol file: 19914-38-6.mol

Synonyms:Alanine,N-carboxy-N-methyl-, N-tert-butyl ester, D- (8CI);(2R)-2-[(tert-Butoxycarbonyl)methylamino]propionic acid;N-(tert-Butoxycarbonyl)-N-methyl-D-alanine;N-alpha-t-Boc-N-alpha-methyl-D-alanine;

Chemical Property of BOC-N-methyl-D-alanine

Chemical Property:

• Vapor Pressure: 0.00035mmHg at 25°C
• Melting Point: 88-92 °C
• Refractive Index: 1.466
• Boiling Point: 296.3 °C at 760 mmHg
• PKA: 4.03±0.10(Predicted)
• Flash Point: 133 °C
• PSA: 66.84000
• Density: 1.111 g/cm³
• LogP: 1.32640
• Storage Temp.: −20°C
• Solubility.: soluble in Ethanol
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 203.11575802
• Heavy Atom Count: 14
• Complexity: 232

Purity/Quality:

99% ^*data from raw suppliers

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

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of BOC-N-methyl-D-alanine

There total 4 articles about BOC-N-methyl-D-alanine 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: 96.0%

Boc-(R)-Ala (3744-87-4,7764-95-6,15761-38-3) + methyl iodide (74-88-4) → N-tert-butoxycarbonyl-N-methyl-(R)-alanine (13734-31-1,16948-16-6,19914-38-6)

Guidance literature:

Boc-(R)-Ala; With sodium hydride; In tetrahydrofuran; at 0 ℃; for 1h; Inert atmosphere;

methyl iodide; In tetrahydrofuran; at 0 - 20 ℃; for 24h; Inert atmosphere;

DOI:10.1111/bph.13547

Reference yield:

N-methyl-D-alanine (29475-64-7) + di-tert-butyl dicarbonate (24424-99-5) → N-tert-butoxycarbonyl-N-methyl-(R)-alanine (13734-31-1,16948-16-6,19914-38-6)

Guidance literature:

N-methyl-D-alanine; With sodium hydroxide; In methanol; water; at 0 - 10 ℃; for 0.166667h;

di-tert-butyl dicarbonate; In methanol; water; at 0 - 30 ℃;

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → N-tert-butoxycarbonyl-N-methyl-(R)-alanine (13734-31-1,16948-16-6,19914-38-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium carbonate / water; tetrahydrofuran / 48 h / 0 - 20 °C

2.1: sodium hydride / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere

2.2: 24 h / 0 - 20 °C / Inert atmosphere

With sodium hydride; sodium carbonate; In tetrahydrofuran; water;

DOI:10.1111/bph.13547

upstream raw materials:

N-(tert-butyloxycarbonyl) azide

Boc-(R)-Ala

methyl iodide

di-tert-butyl dicarbonate

Downstream raw materials:

(S)-1-[(R)-2-(tert-Butoxycarbonyl-methyl-amino)-propionyl]-pyrrolidine-2-carboxylic acid benzyl ester

1,1-dimethylethyl ((1R)-2-{[3-({[2-chloro-4-(5-methyl-2-furanyl)phenyl]sulfonyl}amino)-4-(methyloxy)phenyl]amino}-1-methyl-2-oxoethyl)methylcarbamate

Cyclo<(-L-Phe-D-^MeN-Ala-L-Hag-D-^MeN-Ala)2->

2S-[[2R-[N-(tert-butoxycarbonyl)-N-(methyl)amino]propionyl]amino]-N-[2R-hydroxy-3-[[(4-methoxyphenyl)sulfonyl](2-methylpropyl)amino]-1S-(phenylmethyl)propyl]-3,3-dimethylbutanamide

Refernces

• 1、 Mayer,Wimmer,Dillon-Carter,Partilla,Burchardt,Mihovilovic,Baumann,Sitte. "Phase I metabolites of mephedrone display biological activity as substrates at monoamine transporters". supporting information. p. 2657 - 2668. Retrieved 2016/10/19.