BOC-N-ME-SER-OH

Base Information

• Chemical Name: BOC-N-ME-SER-OH
• CAS No.: 101772-29-6
• Molecular Formula: C₉H₁₇NO₅
• Molecular Weight: 219.238
• Hs Code.: 2924299090
• DSSTox Substance ID: DTXSID80426567
• Wikidata: Q72470188
• Mol file: 101772-29-6.mol

Synonyms:N-(tert-butoxycarbonyl)-N-methyl-L-serine;Boc-N-Me-Ser-OH;Boc-N-methyl-L-serine;

Chemical Property of BOC-N-ME-SER-OH

Chemical Property:

• Melting Point: 83-87 °C
• Boiling Point: 353.2 °C at 760 mmHg
• PKA: 3.63±0.10(Predicted)
• Flash Point: 167.4 °C
• PSA: 87.07000
• Density: 1.215 g/cm³
• LogP: 0.29880
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 219.11067264
• Heavy Atom Count: 15
• Complexity: 245

Purity/Quality:

98+% ^*data from raw suppliers

Boc-N-methyl-L-serine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N(C)C(CO)C(=O)O
• Isomeric SMILES: CC(C)(C)OC(=O)N(C)[C@@H](CO)C(=O)O
• Uses: N-Boc-N-methyl-L-serine is used as a precursor in organic synthesis and pharmaceuticals. Boc-N-Me-Ser-OH, is an amino acid building block used in peptide synthesis. With a growing peptide drug market the fast, reliable synthesis of peptides is of great importance.

Technology Process of BOC-N-ME-SER-OH

There total 2 articles about BOC-N-ME-SER-OH 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: 90.0%

(S)-N-(tert-butoxycarbonyl)serine (3262-72-4) + methyl iodide (74-88-4) → (S)-2-((tert-butoxycarbonyl)(methyl)amino)-3-hydroxypropanoic acid (101772-29-6)

Guidance literature:

With sodium hydride; In tetrahydrofuran; at 0 - 20 ℃; for 26h; Inert atmosphere;

DOI:10.1007/s00044-016-1555-5

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → (S)-2-((tert-butoxycarbonyl)(methyl)amino)-3-hydroxypropanoic acid (101772-29-6)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydroxide / 1,4-dioxane; water / 2 h / 0 °C

2: sodium hydride / tetrahydrofuran / 26 h / 0 - 20 °C / Inert atmosphere

With sodium hydride; sodium hydroxide; In tetrahydrofuran; 1,4-dioxane; water;

DOI:10.1007/s00044-016-1555-5

Reference yield:

(S)-2-((tert-butoxycarbonyl)(methyl)amino)-3-hydroxypropanoic acid (101772-29-6) → (S)-3-(2-aminophenoxy)-2-((tertbutoxycarbonyl)(methyl)amino)propanoic acid

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydride / tetrahydrofuran / 7 h / 20 °C / Inert atmosphere

2: palladium on activated charcoal; hydrogen / methanol; tetrahydrofuran / 14 h / Inert atmosphere

With palladium on activated charcoal; hydrogen; sodium hydride; In tetrahydrofuran; methanol;

DOI:10.1021/acs.jmedchem.6b01751

upstream raw materials:

(S)-N-(tert-butoxycarbonyl)serine

methyl iodide

di-tert-butyl dicarbonate

Downstream raw materials:

2-(tert-butoxycarbonyl-methyl-amino)-3-(4-phenoxy-benzenesulfonyl)-propionic acid methyl ester

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