N-(tert-Butoxycarbonyl)-L-phenylalanin
L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-
Grundinformationen
- CAS
13734-34-4- Standard-SMILES
CC(C)(C)OC(=O)N[C@@H](Cc1ccccc1)C(=O)O- InChIKey
ZYJPUMXJBDHSIF-NSHDSACASA-N- Summenformel
- C14H19NO4
- Durchschnittliche Molmasse
- 265,3 g/mol
- Monoisotopische Masse
- 265,13140809
Namen und Bezeichner
- Bevorzugter Name
- L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-
- IUPAC
- (2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoic acid
- Lokaler Name
- N-(tert-Butoxycarbonyl)-L-phenylalanin
- Englischer Name
- N-(tert-Butoxycarbonyl)-L-phenylalanine
- Summenformel
- C14H19NO4
- Molmasse
- 265.3
Namen und Synonyme
N-(tert-Butoxycarbonyl)-L-phenylalanineN-t-Butyloxycarbonyl-L-phenylalanineN-tert-Butyloxycarbonyl-L-phenylalanineL-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-NSC 111172EINECS 237-305-5N-(tert-Butoxycarbonyl)phenylalanineAlanine, N-carboxy-3-phenyl-, N-tert-butyl ester, L-DTXSID90884634L-Phenylalanine, N-((1,1-dimethylethoxy)carbonyl)-N-((1,1-Dimethylethoxy)carbonyl)-N-L-phenylalanineN-[(1,1-Dimethylethoxy)carbonyl]-N-L-phenylalanine
Weitere Namen anzeigen
BOC-PHEBOC-L-PHE-OHBOC-L-PHEN-BOC-L-PHENYLALANINEBOC-ph-OHBOC Phenly Alanine
RefChem:797353DTXCID701024064Alanine, N-carboxy-3-phenyl-, N-tert-butyl ester, L-(8CI)237-305-513734-34-4Boc-Phe-OHBoc-L-phenylalanineBoc-phenylalanine
Datenbank-Bezeichner
- CAS
13734-34-4- PubChem CID
- 77857
- DTXSID
DTXSID90884634- ChEMBL
CHEMBL1222330- EC Number
- 237-305-5
- Nikkaji
- J124.089G
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 2,2
- Polarare Oberfläche (TPSA)
- 75,6 Ų
- H-Brücken-Donoren
- 2
- H-Brücken-Akzeptoren
- 4
- Frei drehbare Bindungen
- 6
- Schwere Atome
- 19
- Formalladung
- 0
- Komplexität
- 316
Physikochemische Eigenschaften
- Schmelzpunkt
- 85 · 85-87 °C(lit.)
- Siedepunkt
- 408.52 °C · 408.52°C (rough estimate)
- Dichte
- 1.1356 · 1.1356 (rough estimate)
- Brechungsindex
- 24.5 ° · 24.5 ° (C=1, EtOH)
- storage temp.
- Keep in dark place,Sealed in dry,Room Temperature
- Löslichkeit
- -2 · Soluble in methanol, dichloromethane, dimethylformamide and N-methyl-2-pyrrolidone.
- pka
- 3.88 · 3.88±0.10(Predicted)
- Aggregatzustand
- Fine Crystalline Powder
- Farbe
- White
- BRN
- 2219729 · 2219729
- Major Application
- 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
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
GHS-Klassifizierung
GHS Classification
This chemical does not meet GHS hazard criteria for 30% (3 of 10) of reports.
Warning
H302 (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.
Gefahrenhinweise
Hazard Classes and CategoriesAcute Tox. 4 (30%)
Sicherheitsdaten
- wgk
- 3
- tsca
- TSCA listed
- hs_code
- 29242990
- risk_code
- 36-22-36/37/38-20/21/22
- hazard_code
- Xn,Xi
- safety_code
- 39-26-36-24/25
- Speicherklasse
- 11 - Combustible Solids
Chemie und Industrie
Verwendung und Herstellung
General Manufacturing InformationL-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-: INACTIVE
Anwendungen
VerwendenN-(tert-Butoxycarbonyl)-L-phenylalanine is used in enantioselective hydrolysis of amino acid esters. Acts as an inhibitor of gastric acid secretion.
Darstellung
synthetischeSodium 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).
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