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Sodium Carbonate → HCID 44517832, Verbindung

HRID 1951122
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1951122
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:12][N:11]([C:13]([CH:15]3[CH2:20][CH2:19][N:18]([CH2:21][CH2:22][CH2:23]SC)[CH2:17][CH2:16]3)=[O:14])[CH2:10][CH:9]2[N:26]([CH3:41])[C:27](=[O:40])[C:28]2[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[C:30]([C:36]([F:39])([F:38])[F:37])[CH:29]=2)=[CH:4][CH:3]=1.Cl[C:43]1C=CC=C(C(OO)=O)C=1.[S:53](=[O:57])(=O)(O)[O-:54].[Na+].C(=O)([O-])[O-].[Na+].[Na+]>ClCCl.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[CH2:12][N:11]([C:13]([CH:15]3[CH2:16][CH2:17][N:18]([CH2:21][CH2:22][CH2:23][S:53]([CH3:43])(=[O:57])=[O:54])[CH2:19][CH2:20]3)=[O:14])[CH2:10][CH:9]2[N:26]([CH3:41])[C:27](=[O:40])[C:28]2[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[C:30]([C:36]([F:37])([F:39])[F:38])[CH:29]=2)=[CH:6][CH:7]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 10340Sodium CarbonateHCID 70297m-Chloroperbenzoic acidHCID 516919Sodium BisulfateHCID 67025603HCID 67025603, Verbindung

Produkt 1

HCID 44517832HCID 44517832, VerbindungAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962
Water
Lösungsmittel
HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of N-{(3RS,4SR)-4-(4-chloro-phenyl)-1-[1-(3-methylsulfanyl-propyl)-piperidine-4-carbonyl]-pyrrolidin-3-yl}-4-methoxy-N-methyl-3-trifluoromethyl-benzamide (80 mg, 0.13 mmol) in dichloromethane (2 mL) was added under an atmosphere of nitrogen m-chloroperbenzoic acid (47 mg, 0.27 mmol) and stirred for 3 d at ambient temperature. Further addition of m-chloroperbenzoic acid (47 mg, 0.27 mmol) was followed by stirring for 3 h at ambient temperature. After the addition of an aqueous saturated solution of sodium bisulfate (10 mL) and water (10 mL) it was stirred for 1 h at ambient temperature. The reaction mixture was basified by addition of an aqueous solution of sodium carbonate (1 M). The aqueous layer was extracted with dichloromethane (20 mL) and the organic layers were washed with water (15 mL) and dried over sodium sulfate. Purification by chromatography (SiO2, heptane:(ethyl acetate:triethylamine=95:5):methanol=20:80:0 to 0:85:15) afforded the title compound (70 mg, 83%) as a light brown oil. MS m/e: 644.2 [M]+.

Aufarbeitung

  1. stirringby stirring for 3 h at ambient temperature
  2. stirringwas stirred for 1 h at ambient temperature
  3. extractionThe aqueous layer was extracted with dichloromethane (20 mL)
  4. washthe organic layers were washed with water (15 mL)
  5. dry with materialdried over sodium sulfate
  6. customPurification by chromatography (SiO2, heptane:(ethyl acetate:triethylamine=95:5):methanol=20:80:0 to 0:85:15)

Quellen und Nachweise

ORD-Eintrag
ord-5ef31a8228e74b8485b2fbde7fa65ca5
Quelldatensatz
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08404679B2

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