Ammonia → 8-Carbamyl-5-(3-(7-chloroquinolin-2-ylmethoxy)phenyl)-4,6-dithiaoctanoic acid

HRID 232414

Reaktionsgleichung

[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH2:12][O:13][C:14]3[CH:15]=[C:16]([CH:20]([S:27][CH2:28][CH2:29][C:30](O)=[O:31])[S:21][CH2:22][CH2:23][C:24]([OH:26])=[O:25])[CH:17]=[CH:18][CH:19]=3)=[N:9]2)=[CH:4][CH:3]=1.C([N:35](CC)CC)C.[I-].ClC1C=CC=C[N+]=1C.N>C(Cl)Cl.CC#N.O>[C:30]([CH2:29][CH2:28][S:27][CH:20]([C:16]1[CH:17]=[CH:18][CH:19]=[C:14]([O:13][CH2:12][C:8]2[CH:7]=[CH:6][C:5]3[C:10](=[CH:11][C:2]([Cl:1])=[CH:3][CH:4]=3)[N:9]=2)[CH:15]=1)[S:21][CH2:22][CH2:23][C:24]([OH:26])=[O:25])(=[O:31])[NH2:35]

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

The diacid (Example 3) (3.954 g, 8.04 mmoles) was dissolved in 250 mL CH2Cl2 :CH3CN 4:1. Triethylamine (2.5 mL, 2.2 equiv.) was added followed, at 0° C., by 2-chloro-1-methylpyridinium iodide (2.257 g, 1.1 equiv.). After stirring 1 hour at 0° C., ammonia was added and the mixture stirred for another hour at 10° C. Water was then added and the aqueous layer acidified to pH 5. Extraction with CH2Cl2 (2×) and EtOAc (2×) and the flash chromatography of the residue on silica with acetone:CH2Cl2 :AcOH 40:60:1 and 50:50:1 afforded the title compound.

Aufarbeitung

stirringthe mixture stirred for another hour at 10° C
extractionExtraction with CH2Cl2 (2×) and EtOAc (2×)

Quellen und Nachweise

ORD-Eintrag: ord-841a44b99eeb4eb2a9bd3a5a207879ec
Quelldatensatz: uspto-grants-1989_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US04851409

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