2-Tert-butoxycarbonylamino-3-naphthalen-2-YL-propionic acid

Base Information

• Chemical Name: 2-Tert-butoxycarbonylamino-3-naphthalen-2-YL-propionic acid
• CAS No.: 56583-58-5
• Molecular Formula: C₁₈H₂₁NO₄
• Molecular Weight: 315.369
• DSSTox Substance ID: DTXSID40394617
• Mol file: 56583-58-5.mol

Synonyms:56583-58-5;2-((tert-Butoxycarbonyl)amino)-3-(naphthalen-2-yl)propanoic acid;2-TERT-BUTOXYCARBONYLAMINO-3-NAPHTHALEN-2-YL-PROPIONIC ACID;N-T-BOC-D-3-(2-NAPHTHYL)ALANINE;2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-naphthalen-2-ylpropanoic acid;2-tert-butoxycarbonylamino-3-naphthalen-2-ylpropanoic acid;BOC-3-(2-NAPHTHYL)-ALANINE;Boc-2-D-Nal-OH;BOC-D-2-NAPHTHYLALANINE;N-Boc-3-(2-naphthyl)-D-alanine;N-Boc-3-(2-naphthyl)-L-alanine;MFCD00076900;MFCD00079671;SCHEMBL1519731;DTXSID40394617;URKWHOVNPHQQTM-UHFFFAOYSA-N;2-(tert-butoxycarbonylamino)-3-(naphthalen-2-yl)propanoic acid;MFCD01883037;AB02910;AB03049;DS-3300;SY032860;SY035282;CS-0173241;FT-0629974;FT-0655357;FT-0724326;Y11282;2-tert-Butoxycarbonylamino-3-(2-naphtyl)propionic acid;2-tert-butoxycarbonylamino-3-naphthalen-2-yl-propanoic acid;2-{[(tert-butoxy)carbonyl]amino}-3-(naphthalen-2-yl)propanoic acid;2-((tert-Butoxycarbonyl)amino)-3-(naphthalen-2-yl)propanoic acid (Boc-DL-2Nal-OH)

Chemical Property of 2-Tert-butoxycarbonylamino-3-naphthalen-2-YL-propionic acid

Chemical Property:

• Vapor Pressure: 2.58E-11mmHg at 25°C
• Melting Point: 92-95oC(lit.)
• Boiling Point: 512.2oC at 760 mmHg
• Flash Point: 263.6oC
• Density: 1.2 g/cm3
• Storage Temp.: −20°C
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 315.14705815
• Heavy Atom Count: 23
• Complexity: 429

Purity/Quality:

99.90% ^*data from raw suppliers

boc-3-(2-naphthyl)-dl-alanine 95 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(CC1=CC2=CC=CC=C2C=C1)C(=O)O

Technology Process of 2-Tert-butoxycarbonylamino-3-naphthalen-2-YL-propionic acid

There total 17 articles about 2-Tert-butoxycarbonylamino-3-naphthalen-2-YL-propionic 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: 93.4%

(RS)-S-ethyl 2-(tert-butoxycarbonylamino)-3-(naphthalen-2-yl)propanethioate (1393112-51-0) → C20H25NO3S + N-tert-butoxycarbonyl-3-(2-naphthyl)-L-alanine (56583-58-5,76985-10-9,58438-04-3)

Guidance literature:

With alcalase CLEA; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tert-butyl alcohol; at 37 ℃; for 696h; optical yield given as %ee; enantioselective reaction; Resolution of racemate; Enzymatic reaction;

DOI:10.1016/j.tetasy.2012.06.020

Reference yield: 93.0%

di-tert-butyl dicarbonate (24424-99-5) + L-3-(2-naphthyl)alanine (6960-34-5,14108-60-2,58438-03-2,76985-09-6,106107-92-0) → N-tert-butoxycarbonyl-3-(2-naphthyl)-L-alanine (56583-58-5,76985-10-9,58438-04-3)

Guidance literature:

With sodium hydroxide; In 1,4-dioxane; pH 10;

DOI:10.1016/0223-5234(91)90056-S

Reference yield: 82.0%

L-3-(2-naphthyl)alanine (6960-34-5,14108-60-2,58438-03-2,76985-09-6,106107-92-0) + 2-(tert-butoxycarbonyloxyimino)-2-phenylacetonitrile (74651-77-7) → N-tert-butoxycarbonyl-3-(2-naphthyl)-L-alanine (56583-58-5,76985-10-9,58438-04-3)

Guidance literature:

With triethylamine; In 1,4-dioxane; water;

upstream raw materials:

di-tert-butyl dicarbonate

L-3-(2-naphthyl)alanine

acetylamino-[2]naphthylmethyl-malonic acid diethyl ester

(S)-N-acetyl-3-(2-naphthyl)alanine

Downstream raw materials:

3,5-dimethylbenzyl (2S)-2-t-butyloxycarbonylamino-3-(2-naphthyl)propionate

[(S)-2-Naphthalen-2-yl-1-((S)-1-phenyl-ethylcarbamoyl)-ethyl]-carbamic acid tert-butyl ester

(2S)-2-[(tert-butoxy)carbonylamino]-3-(2-naphthyl)-N-benzylpropanamide

[(2-tert-butoxycarbonylamino-3-naphthalen-2-yl-propionyl)-(3-phenyl-propyl)-amino]-acetic acid methyl ester

Refernces

• 1、 Hori, Masahiro,Sakakura, Akira,Ishihara, Kazuaki. "Enantioselective 1,3-dipolar cycloaddition of azomethine imines with propioloylpyrazoles induced by chiral π-cation catalysts". supporting information. p. 13198 - 13201. Retrieved 2015/03/30.
• 2、 Tamamura, Hirokazu,Araki, Takanobu,Ueda, Satoshi,Wang, Zixuan,Oishi, Shinya,Esaka, Ai,Trent, John O.,Nakashima, Hideki,Yamamoto, Naoki,Peiper, Stephen C.,Otaka, Akira,Fujii, Nobutaka. "Identification of novel low molecular weight CXCR4 antagonists by structural tuning of cyclic tetrapeptide scaffolds". . p. 3280 - 3289. Retrieved 2007/10/03.