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

HRID 22593

Reaktionsgleichung

Reaktionsgleichung von HRID 22593
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH2:12][S:13][C:14]3[CH:15]=[C:16]([CH:20]([S:27][CH2:28][CH2:29][C:30]([OH:32])=O)[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.[I-].ClC1C=CC=C[N+:36]=1C.C(N(CC)CC)C.N>ClCCl.C(#N)C.CCOCC>[C:30]([CH2:29][CH2:28][S:27][CH:20]([C:16]1[CH:17]=[CH:18][CH:19]=[C:14]([S: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:32])[NH2:36]

Komponenten

8

Edukt 4

HCID 222AmmoniaHCID 8471TriethylamineHCID 1670692-Chloro-1-methylpyridinium iodideHCID 104139205-(3-(7-Chloroquinolin-2-ylmethylthio)phenyl)-4,6-dithianonanedioic acid

Produkt 1

HCID 199305208-Carbamyl-5-(3-(7-chloroquinolin-2-ylmethylthio)phenyl)-4,6-dithiaoctanoic acid

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 3283Diethyl EtherLösungsmittelHCID 6342AcetonitrileLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  1. washit was washed
  2. extractionextracted with ethyl acetate
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customPurification by chromatography

Quellen und Nachweise

ORD-Eintrag
ord-32fdaef34b434ee89b0bff3ed1e90296
Quelldatensatz
uspto-grants-1995_06
Patentnummer
US05428171

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