1-(tert-Butyl)hydrogen-(S)-pyrrolidin-1,2-dicarboxylat
1,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)-
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Grundinformationen
- CAS
15761-39-4- Standard-SMILES
CC(C)(C)OC(=O)N1CCC[C@H]1C(=O)O- InChIKey
ZQEBQGAAWMOMAI-ZETCQYMHSA-N- Summenformel
- C10H17NO4
- Durchschnittliche Molmasse
- 215,25 g/mol
- Monoisotopische Masse
- 215,11575802
Namen und Bezeichner
- Bevorzugter Name
- 1,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)-
- IUPAC
- (2S)-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid
- Lokaler Name
- 1-(tert-Butyl)hydrogen-(S)-pyrrolidin-1,2-dicarboxylat
- Englischer Name
- BOC-L-Proline
- Summenformel
- C10H17NO4
- Molmasse
- 215.25
Namen und Synonyme
Boc-L-prolineN-(tert-Butoxycarbonyl)-L-prolineN-(tert-Butyloxycarbonyl)-L-prolinetert-Butoxycarbonyl-L-proline1-tert-Butoxycarbonyl-L-proline1-tert-Butyloxycarbonyl-L-prolineN-tert-Butoxycarbonylprolinetert-Butyloxycarbonyl-L-prolineNSC 1646601,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)-EINECS 239-848-31,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (S)-
Weitere Namen anzeigen
BOC-PRO-OH(tert-butoxycarbonyl)-L-prolineBOC-PRON-BOC-L-PROLINE(tert-butoxycarbonyl)prolineBOC-L-PROBOC-L-PRO-OHN-BOC-PROLINE(2S)-1-tert-butoxycarbonylpyrrolidine-2-carboxylic acid
1,2-Pyrrolidinedicarboxylic acid, 1-tert-butyl ester, L-1-(tert-Butyl) hydrogen (S)-pyrrolidine-1,2-dicarboxylateDTXSID00884847RefChem:412214DTXCID5010242681,2-Pyrrolidinedicarboxylic acid, 1-tert-butyl ester, L-(8CI)1,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (S)-(9CI)239-848-3
Eigenschaften
Berechnete StruktureigenschaftenWird ergänzt
- XLogP
- 1,5
- Polarare Oberfläche (TPSA)
- 66,8 Ų
- H-Brücken-Donoren
- 1
- H-Brücken-Akzeptoren
- 4
- Frei drehbare Bindungen
- 3
- Schwere Atome
- 15
- Formalladung
- 0
- Komplexität
- 269
Physikochemische Eigenschaften
- Schmelzpunkt
- 133 · 133-135 °C(lit.)
- Siedepunkt
- 355.52 °C · 355.52°C (rough estimate)
- Dichte
- 1.1835 · 1.1835 (rough estimate)
- Brechungsindex
- -60 ° · -60 ° (C=2, AcOH)
- storage temp.
- Keep in dark place,Sealed in dry,Room Temperature
- Löslichkeit
- Soluble in acetic acid.
- Aggregatzustand
- Crystals or Crystalline Powder
- pka
- 4.01 · 4.01±0.20(Predicted)
- Farbe
- White
- BRN
- 15828 · 15828
- Major Application
- peptide synthesis
- InChI
- 1S/C10H17NO4/c1-10(2,3)15-9(14)11-6-4-5-7(11)8(12)13/h7H,4-6H2,1-3H3,(H,12,13)/t7-/m0/s1
- InChIKey
- ZQEBQGAAWMOMAI-ZETCQYMHSA-N
- SMILES
- CC(C)(C)OC(=O)N1CCC[C@H]1C(O)=O
- CAS Datenbank
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 75% (6 of 8) of all reports.
Warning
H315 (25%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 8 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Gefahrenhinweise
Hazard Classes and CategoriesSkin Irrit. 2 (25%)
Sicherheitsdaten
- wgk
- 3
- tsca
- TSCA listed
- hs_code
- 2933990099
- risk_code
- 20/21/22-36/37/38
- hazard_code
- Xn
- safety_code
- 24/25-36-26
- hazard_class
- IRRITANT
- Speicherklasse
- 11 - Combustible Solids
Chemie und Industrie
Verwendung und Herstellung
General Manufacturing Information1,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)-: ACTIVE
Anwendungen
BeschreibungN-Boc-L-proline is a synthetic intermediate. It has been used in the synthesis of enantioselective catalysts for aldol reactions and hepatitis C virus (HCV) NS5A inhibitors.
VerwendenN-Boc-L-proline is used as an intermediate in organic synthesis. It is also used to prepare daclatasvir, which inhibits the hepatitis C virus (HCV) non-structural 5A (NS5A) protein. Further, it is used as a drug in the treatment of hepatitis C virus (HCV).
Darstellung
synthetischeTriethylamine (16.5 mL, 0.12 mmol) was added dropwise over a period of 10 min to a stirred, ice-cold suspension of l-proline (10.0 g, 8.7 mmol) in dichloromethane (200 mL) in a 500-mL three-necked, round-bottomed flask. A solution of Boc2O (28.3 g, 0.13 mmol) in dichloromethane (100 mL) was then added over a period of 10 min and the mixture was stirred for 2.5 h. Thereafter, 10% aqueous citric acid (50 mL) was added, and the dichloromethane layer was washed with saturated brine (2×50 mL) and with water (50 mL). After drying the organic phase over magnesium sulfate, the solvent was evaporated and the residue was taken up in hot ethyl acetate. Dilution of this solution with hexane gave the product, N-tertbutoxycarbonyl- L-proline (17.8 g, 95%); mp 138–140℃; TLC (silica gel): Rf=0:36 (EtOAc/MeOH, 1:1).
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