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m-Chloroperbenzoic acid → HCID 90308809, Verbindung

HRID 2283664
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2283664
C1C=C(Cl)C=C(C(OO)=O)C=1.[S:12]1[CH:16]=[CH:15][C:14]2[C:17]([NH:21][C:22]3[N:23]=[C:24](SC)[N:25]=[N:26][C:27]=3[C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:18][CH:19]=[CH:20][C:13]1=2.[C:35]([O:39][C:40](=[O:49])[NH:41][C@H:42]1[CH2:47][CH2:46][CH2:45][CH2:44][C@H:43]1[NH2:48])([CH3:38])([CH3:37])[CH3:36].C(N(C(C)C)CC)(C)C>C(Cl)(Cl)Cl.C(OCC)(=O)C>[S:12]1[CH:16]=[CH:15][C:14]2[C:17]([NH:21][C:22]3[N:23]=[C:24]([NH:48][C@@H:43]4[CH2:44][CH2:45][CH2:46][CH2:47][C@@H:42]4[NH:41][C:40]([O:39][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:49])[N:25]=[N:26][C:27]=3[C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:18][CH:19]=[CH:20][C:13]1=2
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 70297m-Chloroperbenzoic acidHCID 81531DiisopropylethylamineHCID 1514389(1S,2R)-Cyclohexane-1,2-diamine, N1-BOC protectedHCID 90308829HCID 90308829, Verbindung

Produkt 1

HCID 90308809HCID 90308809, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6212
Chloroform
Lösungsmittel
2×
HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of m-CPBA (65 mg) in chloroform (1.5 ml) was added to a solution of ethyl 5-(benzo[b]thiophen-4-ylamino)-3-(methylthio)-1,2,4-triazine-6-carboxylate obtained in the above-described Step 1 (33 mg) in chloroform (1.5 ml), the reaction solution was stirred at room temperature for 10 minutes. Thereafter, tert-butyl((1S,2R)-2-aminocyclohexyl)carbamate (60 mg) and diisopropylethylamine (0.10 ml) were added, and then the reaction solution was stirred at room temperature for 3 hours. The reaction solution was diluted with ethyl acetate and then washed successively with an aqueous sodium bicarbonate solution and a saturated saline solution. After drying over anhydrous sodium sulfate, the solvent was evaporated under vacuum, and then the resultant residue was purified by column chromatography on silica gel (developing solvent:hexane/ethyl acetate) to obtain ethyl 5-(benzo[b]thiophen-4-ylamino)-3-((1R,2S)-2-(tert-butoxycarbonylamino)cyclohexylamino)-1,2,4-triazine-6-carboxylate.

Aufarbeitung

  1. stirringthe reaction solution was stirred at room temperature for 3 hours
  2. washwashed successively with an aqueous sodium bicarbonate solution
  3. dry with materialAfter drying over anhydrous sodium sulfate
  4. customthe solvent was evaporated under vacuum
  5. customthe resultant residue was purified by column chromatography on silica gel (developing solvent:hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-382a6ce8351a46e9ae0e951a7ee9560e
Quelldatensatz
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09145414B2

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