N-(tert-Butoxycarbonyl)-L-phenylalanin
BOC-PHE-OH · BOC-PHE · BOC-L-PHE-OH · BOC-L-PHENYLALANINE · BOC-L-PHE · N-BOC-L-PHENYLALANINE · BOC-PHENYLALANINE · L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-
Identifikatoren & physikalische Daten
| CAS No. | 13734-34-4 |
|---|---|
| Summenformel | C14H19NO4 |
| Durchschnittliche Molmasse | 265,3 g/mol |
| Monoisotopische Masse | 265,13140809 g/mol |
| SMILES | CC(C)(C)OC(=O)N[C@@H](Cc1ccccc1)C(=O)O |
| InChIKey | ZYJPUMXJBDHSIF-NSHDSACASA-N |
| PubChem CID | 77857 |
| ChEMBL | CHEMBL1222330 |
| EC No. | 237-305-5 |
| DTXSID | DTXSID90884634 |
| Lokaler Name | N-(tert-Butoxycarbonyl)-L-phenylalanin |
Chemische & physikalische Eigenschaften
| XLogP | 2,2 |
|---|---|
| Polarare Oberfläche (TPSA) | 75,6 |
| H-Brücken-Donoren | 2 |
| H-Brücken-Akzeptoren | 4 |
| Frei drehbare Bindungen | 6 |
| Schwere Atome | 19 |
| Formalladung | 0 |
| Komplexität | 316 |
| Schmelzpunkt | 85-87 °C(lit.) |
| Siedepunkt | 408.52°C (rough estimate) |
| Dichte | 1.1356 (rough estimate) |
| Brechungsindex | 24.5 ° (C=1, EtOH) |
| Lagerbedingungen | Keep in dark place,Sealed in dry,Room Temperature |
| Löslichkeit | Soluble in methanol, dichloromethane, dimethylformamide and N-methyl-2-pyrrolidone. |
| pKa (Säurekonstante) | 3.88±0.10(Predicted) |
| Aggregatzustand | Fine Crystalline Powder |
| Farbe | White |
| BRN | 2219729 |
| Hauptanwendungen | peptide synthesis |
| InChI | InChI=1S/C14H19NO4/c1-14(2,3)19-13(18)15-11(12(16)17)9-10-7-5-4-6-8-10/h4-8,11H,9H2,1-3H3,(H,15,18)(H,16,17)/t11-/m0/s1 |
| InChIKey | ZYJPUMXJBDHSIF-NSHDSACASA-N |
| SMILES | C(O)(=O)[C@H](CC1=CC=CC=C1)NC(OC(C)(C)C)=O |
| CAS Datenbank | 13734-34-4(CAS DataBase Reference) |
| EPA chemische Informationen | L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]- (13734-34-4) |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 30% (3 of 10) of reports.WarningH302 (30%): Harmful if swallowed [Warning Acute toxicity, oral]P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 10 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Hazard Classes and Categories | Acute Tox. 4 (30%) |
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| Zollcode | 29242990 |
| R-Sätze (R) | 36-22-36/37/38-20/21/22 |
| Gefahrensymbole | Xn,Xi |
| Sicherheitshinweise (S) | 39-26-36-24/25 |
| Lagerklasse | 11 - Combustible Solids |
Anwendungen & Verwendung
Verwenden
N-(tert-Butoxycarbonyl)-L-phenylalanine is used in enantioselective hydrolysis of amino acid esters. Acts as an inhibitor of gastric acid secretion.
Herstellung & Synthese
synthetische
Sodium hydroxide (4.4 g, 0.11 mol) was placed in a flask, and dissolved in water (110 mL). Phenylalanine (16.5 g, 0.1 mol) was added, the suspension was stirred until a solution was obtained, and then tert-butanol (75 mL) was added. Boc2O (22.3 g, 0.12 mol) was then added with stirring over a period of 1 h, keeping the mixture near 0 ℃. A white precipitate was produced, and at the end of the addition the pH had dropped to 7.5–8.5. The mixture was then carefully acidified by the slow, continuous addition of saturated citric acid to give the product N-tert-butoxycarbonyl-L-phenylalanine (21.5 g, 81%); mp 85℃; [a]21D = t25:5 (c = 1, ethanol).