Reaktion #50871

ord-32fdaef34b434ee89b0bff3ed1e90296

Reaktionsgleichung

CCN(CC)CC
triethylamine
N
ammonia
O=C(O)CCSC(SCCC(=O)O)c1cccc(SCc2ccc3ccc(Cl)cc3n2)c1
diacid
O=C(O)CCSC(SCCC(=O)O)c1cccc(SCc2ccc3ccc(Cl)cc3n2)c1
5-(3-(7-chloroquinolin-2-ylmethylthio)phenyl)-4,6-dithianonanedioic acid
C[n+]1ccccc1Cl.[I-]
2-chloro-1-methylpyridinium iodide
→
NC(=O)CCSC(SCCC(=O)O)c1cccc(SCc2ccc3ccc(Cl)cc3n2)c1
title compound
NC(=O)CCSC(SCCC(=O)O)c1cccc(SCc2ccc3ccc(Cl)cc3n2)c1
8-CARBAMYL-5-(3-(7-CHLOROQUINOLIN-2-YLMETHYLTHIO)PHENYL)-4,6-DITHIAOCTANOIC ACID

Edukte

—
saturated solution
CCN(CC)CC
triethylamine
N
ammonia
O=C(O)CCSC(SCCC(=O)O)c1cccc(SCc2ccc3ccc(Cl)cc3n2)c1
diacid
O=C(O)CCSC(SCCC(=O)O)c1cccc(SCc2ccc3ccc(Cl)cc3n2)c1
5-(3-(7-chloroquinolin-2-ylmethylthio)phenyl)-4,6-dithianonanedioic acid
C[n+]1ccccc1Cl.[I-]
2-chloro-1-methylpyridinium iodide

Reagenzien

Keine

Lösungsmittel

CCOCC
ether
ClCCl
dichloromethane
CC#N
acetonitrile

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Waschenit was washed
  2. 2
    Extraktionextracted with ethyl acetate
  3. 3
    Trocknendried over sodium sulfate
  4. 4
    Filtrationfiltered
  5. 5
    Sonstigeevaporated to dryness
  6. 6
    SonstigePurification by chromatography

Vorschrift

To 500 mg of diacid (Example 20, Step 4) in dichloromethane (39 mL) and acetonitrile (9.9 mL) at 0° C. was added 2-chloro-1-methylpyridinium iodide (315 mg). After 15 min triethylamine (170 μL) and 10 mL of a saturated solution of ammonia in ether were added. The solution was stirred 1 hr at room temperature then it was washed with acidified 25% ammonium acetate, extracted with ethyl acetate, dried over sodium sulfate, filtered and evaporated to dryness. Purification by chromatography afforded the title compound.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05428171uspto-grants-1995_06