1-(tert-Butyl)hydrogen-(S)-pyrrolidin-1,2-dicarboxylat

1,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)-

HCID 85083CAS 15761-39-4

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Grundinformationen

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

Datenbank-Bezeichner

CAS: 15761-39-4
PubChem CID: 85083
DTXSID: DTXSID00884847
ChEMBL: CHEMBL1221957
EC Number: 239-848-3
Nikkaji: J208.113J

Eigenschaften

Berechnete Struktureigenschaften

XLogP: 1,5
Polarare Oberfläche (TPSA): 66,8 Å²
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: 15761 · 15761-39-4(CAS DataBase Reference)
EPA chemische Informationen: 1 · 1,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)- (15761-39-4)

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 5 Einträge

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: 2933 99 80
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 · 2 Einträge

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 · 1 Eintrag

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).