15-(Boc-amino)-4,7,10,13-tetraoxapentadecanoic acid

Base Information

• Chemical Name: 15-(Boc-amino)-4,7,10,13-tetraoxapentadecanoic acid
• CAS No.: 756525-91-4
• Molecular Formula: C16H31 N O8
• Molecular Weight: 365.424
• Hs Code.: 29225090
• DSSTox Substance ID: DTXSID60373186
• Wikidata: Q72507837
• Mol file: 756525-91-4.mol

Synonyms:756525-91-4;t-Boc-N-amido-PEG4-acid;15-(Boc-amino)-4,7,10,13-tetraoxapentadecanoic acid;2,2-Dimethyl-4-oxo-3,8,11,14,17-pentaoxa-5-azaicosan-20-oic acid;Boc-NH-PEG4-CH2CH2COOH;3-[2-[2-[2-[2-[(2-methylpropan-2-yl)oxycarbonylamino]ethoxy]ethoxy]ethoxy]ethoxy]propanoic Acid;(Boc-amino)-PEG4-carboxylic Acid;Carboxy-PEG4-(Boc-amine);5,8,11,14-Tetraoxa-2-azaheptadecanedioic acid 1-(1,1-dimethylethyl) ester;MFCD07781254;BOC-15-AMINO-4,7,10,13-TETRAOXAPENTADECANOIC ACID;C16H31NO8;t-boc-N-amido-PEG4-propionic acid;SCHEMBL436333;LCZC1174;DTXSID60373186;YEIYIPDFZMLJQH-UHFFFAOYSA-N;BCP30519;EX-A3894;ZB0941;AKOS022182023;CS-W020872;HY-W040132;SB83702;s10745;BP-21635;DS-15585;SY066345;B5665;EN300-6488376;A865643;1-{[(tert-butoxy)carbonyl]amino}-3,6,9,12-tetraoxapentadecan-15-oic acid;15-[(tert-Butoxycarbonyl)amino]-4,7,10,13-tetraoxapentadecanoic Acid;15-T-BUTYLOXYCARBONYLAMINO-4,7,10,13-TETRAOXA-PENTADECANOIC ACID;2,2-Dimethyl-4-oxo-3,8,11,14,17-pentaoxa-5-azaicosan-20-oicacid;N-(tert-Butyloxycarbonyl)-15-amino-4,7,10,13-tetraoxapentanedecanoic acid;15-(Boc-amino)-4,7,10,13-tetraoxapentadecanoic acid, purum, >=97.0% (TLC);3-(2-{2-[2-(2-tert-butoxycarbonylamino-ethoxy)-ethoxy]-ethoxy}-ethoxy)-propionic acid;3-[2-(2-{2-[2-((tert-butoxycarbonyl)amino)ethoxy]ethoxy}ethoxy)ethoxy]propanoic acid;Boc-15-Amino-4,7,10,13-tetraoxapentadecanoic acid pound>> Boc-NH-PEG4-CH2CH2COOH pound>>15-(Boc-aMino)-4,7,10,13-tetraoxapentadecanoic acid

Chemical Property of 15-(Boc-amino)-4,7,10,13-tetraoxapentadecanoic acid

Chemical Property:

• Boiling Point: 504.5±50.0 °C(Predicted)
• PKA: 4.28±0.10(Predicted)
• PSA: 112.55000
• Density: 1.124±0.06 g/cm3 (20 ºC 760 Torr)
• LogP: 1.44310
• Storage Temp.: 2-8°C
• XLogP3: -0.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 17
• Exact Mass: 365.20496695
• Heavy Atom Count: 25
• Complexity: 357

Purity/Quality:

98%,99%, ^*data from raw suppliers

Boc-15-amino-4,7,10,13-tetraoxapentadecanoic acid ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NCCOCCOCCOCCOCCC(=O)O
• Description: t-Boc-N-amido-PEG4-acid is a PEG linker containing a terminal carboxylic acid and Boc-protected amino group. The hydrophilic PEG spacer increases solubility in aqueous media. The terminal carboxylic acid can react with primary amine groups in the presence of activators (e.g. EDC, HATU) to form a stable amide bond. The Boc group can be deprotected under mild acidic conditions to form the free amine.
• Uses: 15-(Boc-amino)-4,7,10,13-tetraoxapentadecanoic acid is used as a substitution variant of cocaine esterase with improved stability and its use in treatment of cocaine overdose.

Technology Process of 15-(Boc-amino)-4,7,10,13-tetraoxapentadecanoic acid

There total 3 articles about 15-(Boc-amino)-4,7,10,13-tetraoxapentadecanoic 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%

benzyl (E)-2,2-dimethyl-4-oxo-3,8,11,14,17-pentaoxa-5-azaicos-18-en-20-oate → 3-[2-[2-[2-[2-(tert-butoxycarbonylamino)ethoxy]ethoxy]ethoxy]ethoxy]propanoic acid (756525-91-4)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In tetrahydrofuran; for 24h; under 760.051 Torr;

DOI:10.1002/jlcr.3816

Reference yield: 93.0%

3-[2-(2-{2-[2-(2-aminoethoxy)ethoxy]ethoxy}ethoxy)ethoxy]propanoic acid (663921-15-1) + di-tert-butyl dicarbonate (24424-99-5) → 3-[2-[2-[2-[2-(tert-butoxycarbonylamino)ethoxy]ethoxy]ethoxy]ethoxy]propanoic acid (756525-91-4)

Guidance literature:

With potassium carbonate; In tetrahydrofuran; water; at 20 ℃; Cooling with ice;

Reference yield:

2-<2-<2-<2-<(tert-Butoxycarbonyl)amino>ethoxy>ethoxy>ethoxy>ethanol (106984-09-2) → 3-[2-[2-[2-[2-(tert-butoxycarbonylamino)ethoxy]ethoxy]ethoxy]ethoxy]propanoic acid (756525-91-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 4-methyl-morpholine / dichloromethane / 18 h / 20 °C

2: palladium 10% on activated carbon; hydrogen / tetrahydrofuran / 24 h / 760.05 Torr

With 4-methyl-morpholine; palladium 10% on activated carbon; hydrogen; In tetrahydrofuran; dichloromethane;

DOI:10.1002/jlcr.3816

upstream raw materials:

2-<2-<2-<2-<(tert-Butoxycarbonyl)amino>ethoxy>ethoxy>ethoxy>ethanol

3-[2-(2-{2-[2-(2-aminoethoxy)ethoxy]ethoxy}ethoxy)ethoxy]propanoic acid

di-tert-butyl dicarbonate

Downstream raw materials:

C₄₄H₇₀N₁₂O₁₃

3-[2-(2-{2-[2-(2-aminoethoxy)ethoxy]ethoxy}ethoxy)ethoxy]propanoic acid

C₂₃H₃₇NO₈

Refernces

• 1、 Song, Fengbin,Chen, Lu,Lin, Ronghui,Salter, Rhys. "Synthesis of carboxy-polyethylene glycol-amine (CA (PEG)n) and [1-14C]-CA (PEG)n via oxa-Michael addition of amino-polyethylene glycols to propiolates vs to acrylates". . p. 15 - 24. Retrieved 2019/12/30.