Boc-3-(2-naphthyl)-D-alanine

Base Information

• Chemical Name: Boc-3-(2-naphthyl)-D-alanine
• CAS No.: 76985-10-9
• Molecular Formula: C18H21NO4
• Molecular Weight: 315.369
• Hs Code.: 29242990
• European Community (EC) Number: 616-417-1
• DSSTox Substance ID: DTXSID10370327
• Nikkaji Number: J1.106.974F
• Wikidata: Q72450140
• Mol file: 76985-10-9.mol

Synonyms:76985-10-9;Boc-3-(2-naphthyl)-D-alanine;Boc-D-2-Nal-OH;N-(tert-Butoxycarbonyl)-3-(2-naphthyl)-D-alanine;(R)-2-((tert-butoxycarbonyl)amino)-3-(naphthalen-2-yl)propanoic acid;BOC-D-2-NAPHTHYLALANINE;(2R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-naphthalen-2-ylpropanoic acid;N-Boc-3-(2-naphthyl)-D-alanine;MFCD00076900;(R)-N-BOC-2-Naphthylalanine;Boc-D-2Nal-OH;SCHEMBL3821361;BOC-D-ALA(2-NAPH)-OH;DTXSID10370327;URKWHOVNPHQQTM-OAHLLOKOSA-N;N-Boc 3-(2-naphthyl)-D-alanine;(2R)-2-(tert-Butoxycarbonylamino)-3-(2-naphthyl)propionic acid;AKOS015909903;AC-7946;AM83703;CS-W008489;FD10531;HY-W008489;DS-15333;N-BOC-2-(2-NAPHTHYL)-D-ALANINE;PD196585;B3616;CS-0046078;Boc-D-2-Nal-OH, >=97.0% (HPLC);M03151;EN300-2010703;A838927;N-TERT-BUTOXYCARBONYL-2-NAPHTHYL-D-ALANINE;(R)-alpha-(Boc-amino)-2-naphthalenepropionic Acid;(2R)-2-tert-Butoxycarbonylamino-3-(2-naphthyl)propionic acid;(R)-alpha-tert-Butoxycarbonylamino-2-naphthalenepropionic Acid;(R)-2-(tert-butoxycarbonylamino)-3-(naphthalen-2-yl)propanoic acid;(2R)-2-{[(tert-butoxy)carbonyl]amino}-3-(naphthalen-2-yl)propanoic acid;(2R)-2-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-3-naphthalen-2-ylpropanoic acid;(2R)-2-[(2-Methylpropan-2-yl)oxycarbonylamino]-3-naphthalen-2-ylpropanoic acid;(R)-2-(tert-Butoxycarbonylamino)-3-(naphthalen-2-yl)propanoic acid (Boc-D-2Nal-OH)

Chemical Property of Boc-3-(2-naphthyl)-D-alanine

Chemical Property:

• Appearance/Colour: off-white granular powder
• Vapor Pressure: 2.58E-11mmHg at 25°C
• Melting Point: 92-95 °C(lit.)
• Refractive Index: 1.5740 (estimate)
• Boiling Point: 512.2 °C at 760 mmHg
• PKA: 3.88±0.30(Predicted)
• Flash Point: 263.6 °C
• PSA: 75.63000
• Density: 1.2 g/cm³
• LogP: 3.75110
• Storage Temp.: −20°C
• Solubility.: Chloroform (Sparingly), Ethanol (Sparingly), Methanol (Slightly)
• 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:

≥98%,≥99%, ^*data from raw suppliers

Boc-3-(2-Naphthyl)-D-alanine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(CC1=CC2=CC=CC=C2C=C1)C(=O)O
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@H](CC1=CC2=CC=CC=C2C=C1)C(=O)O
• Uses: Boc-3-(2-Naphthyl)-D-alanine is a reagent in Lanreotide trisulfide synthesis and somatostatin receptor binding activity. Reagent in the preparation by coupling and structure-activity relationships of arginine containing tripeptides as MC4 receptor ligands.

Technology Process of Boc-3-(2-naphthyl)-D-alanine

There total 27 articles about Boc-3-(2-naphthyl)-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: 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: 93.0%

di-tert-butyl dicarbonate (24424-99-5) + (R)-2-naphthylalanine (76985-09-6,106107-92-0) → Boc-D-2Nal-OH (76985-10-9)

Guidance literature:

With sodium hydroxide; at 30 ℃; for 6h; Large scale;

DOI:10.1021/op050026g

upstream raw materials:

di-tert-butyl dicarbonate

(R)-2-naphthylalanine

2-amino-3-(2-naphthyl)propanoic acid

N-(trifluoroacetyl)-3-(2-naphthyl)-DL-alanine

Downstream raw materials:

C₂₃H₂₉NO₆

(2R)-2-(N-(tert-butoxycarbonyl)-N-methylamino)-3-(2-naphthyl)-propionic acid

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

BOC-(S)-3-(2-naphthyl)alanyl-N-benzyl-N-methylamide

Refernces

• 1、 -. "ARYLPYRROLIDINE DICARBOXYLIC ACID AMIDE DERIVATIVE". Paragraph 0051; 0052; 0053. . Retrieved 2018/12/05.
• 2、 -. "METHOD FOR SYNTHESIZING OPTICALLY ACTIVE α-AMINO ACID USING CHIRAL METAL COMPLEX COMPRISING AXIALLY CHIRAL N-(2-ACYLARYL)-2-[5,7-DIHYDRO-6H-DIBENZO[c,e]AZEPIN-6-YL]ACETAMIDE COMPOUND AND AMINO ACID". Paragraph 0510; 0512; 0513; 0524. . Retrieved 2016/11/17.