2-(Boc-aminomethyl)phenylacetic acid

Base Information

• Chemical Name: 2-(Boc-aminomethyl)phenylacetic acid
• CAS No.: 40851-66-9
• Molecular Formula: C14H19NO4
• Molecular Weight: 265.309
• Hs Code.: 29225090
• European Community (EC) Number: 637-014-7
• DSSTox Substance ID: DTXSID80373143
• Nikkaji Number: J2.426.517J
• Wikidata: Q72448203
• Mol file: 40851-66-9.mol

Synonyms:40851-66-9;2-(BOC-AMINOMETHYL)PHENYLACETIC ACID;2-(2-(((tert-Butoxycarbonyl)amino)methyl)phenyl)acetic acid;BOC-2-AMINOMETHYL-PHENYLACETIC ACID;2-[2-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]phenyl]acetic Acid;2-(2-(N-BOC-AMINOMETHYL)PHENYL)ACETIC ACID;MFCD06656428;BENZENEACETIC ACID, 2-[[[(1,1-DIMETHYLETHOXY)CARBONYL]AMINO]METHYL]-;2-[2-({[(tert-butoxy)carbonyl]amino}methyl)phenyl]acetic acid;2-(Boc-aminomethyl)phenylaceticAcid;2-(2-((tert-butoxycarbonylamino)methyl)phenyl)acetic acid;SCHEMBL825511;(2-{[(tert-butoxycarbonyl)amino]methyl}phenyl)acetic acid;DTXSID80373143;CGPQRFCFBISLKF-UHFFFAOYSA-N;BCP21715;AB3116;Boc-(2-aminomethylphenyl)acetic acid;AKOS015891415;AS-44687;SY004133;CS-0067868;FT-0639675;EN300-112336;2-(Boc-aminomethyl)phenylacetic acid, >=99.0%;2-(tert-butoxycarbonylaminomethyl)phenylacetic acid;2-(tert-Butoxycarbonylaminomethyl)benzeneacetic acid;[2-(tert-butoxycarbonylamino-methyl)-phenyl]-acetic acid

Chemical Property of 2-(Boc-aminomethyl)phenylacetic acid

Chemical Property:

• Vapor Pressure: 2.4E-08mmHg at 25°C
• Refractive Index: 1.533
• Boiling Point: 435.2 °C at 760 mmHg
• PKA: 4.26±0.10(Predicted)
• Flash Point: 217 °C
• PSA: 75.63000
• Density: 1.163 g/cm³
• LogP: 2.72930
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 265.13140809
• Heavy Atom Count: 19
• Complexity: 322

Purity/Quality:

99% ^*data from raw suppliers

Boc-2-aminomethyl-phenylacetic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-36
• Safety Statements: 36

MSDS Files:

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NCC1=CC=CC=C1CC(=O)O
• Uses: [2-(tert-Butoxycarbonylaminomethyl)phenyl]acetic Acid is used to study molecular modeling on oligomers built from 2-aminomethylphenylacetic acid.

Technology Process of 2-(Boc-aminomethyl)phenylacetic acid

There total 8 articles about 2-(Boc-aminomethyl)phenylacetic 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: 98.0%

methyl 2-(N-(tert-butoxycarbonyl)aminomethyl)phenylacetate (147410-31-9) → 2-(tert-butoxycarbonylaminomethyl)phenylacetic acid (40851-66-9)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; water; at 20 ℃;

Reference yield: 88.1%

di-tert-butyl dicarbonate (24424-99-5) + 2-Aminomethylphenylacetic acid (40851-65-8) → 2-(tert-butoxycarbonylaminomethyl)phenylacetic acid (40851-66-9)

Guidance literature:

With water; In 1,4-dioxane; at 0 - 20 ℃; for 3.16667h;

DOI:10.1007/s11164-013-1069-4

Reference yield:

ortho-bromophenylacetic acid (18698-97-0) → 2-(tert-butoxycarbonylaminomethyl)phenylacetic acid (40851-66-9)

Guidance literature:

Multi-step reaction with 5 steps

1: H₂SO₄ / Heating

2: dimethylformamide / Heating

3: H₂; aq. HCl / Pd/C / methanol / 25 °C / 3620.04 Torr

4: Et₃N / tetrahydrofuran / 25 °C

5: aq. LiOH / tetrahydrofuran / 25 °C

With hydrogenchloride; lithium hydroxide; sulfuric acid; hydrogen; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2005.03.020

upstream raw materials:

carbon dioxide

N-(tert-butoxycarbonyl)-2-methylbenzylamine

methyl 2-(N-(tert-butoxycarbonyl)aminomethyl)phenylacetate

ortho-bromophenylacetic acid

Downstream raw materials:

[2-({methyl-[1-(S)-phenyl-2-pyrrolidin-1-yl-ethyl]-carbamoyl}-methyl)-benzyl]-carbamic acid tert-butyl ester

2-Aminomethylphenylacetic acid

2-[2-[[tert-butoxycarbonyl(methyl)amino]methyl]phenyl]acetic acid

C₁₈H₂₇N₅O₄

Refernces

• 1、 Le Bourdonnec, Bertrand,Ajello, Christopher W.,Seida, Pamela R.,Susnow, Roberta G.,Cassel, Joel A.,Belanger, Serge,Stabley, Gabriel J.,DeHaven, Robert N.,DeHaven-Hudkins, Diane L.,Dolle, Roland E.. "Arylacetamide κ opioid receptor agonists with reduced cytochrome P450 2D6 inhibitory activity". . p. 2647 - 2652. Retrieved 2007/10/03.
• 2、 Clark, Robin D.,Jahangir. "PREPARATION OF TETRAHYDROISOQUINOLINES FROM N-(TERT-BUTOXYCARBONYL)-2-METHYLBENZYLAMINES". . p. 1699 - 1703. Retrieved 2007/10/02.