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Triethylamine → 10-(Acetylthiomethyl)-3-t-butoxycarbonylmethyl-2-oxo-1-azacyclodecane

HRID 21977
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 21977
[C:1]([O:5][C:6]([CH2:8][CH:9]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH:12]([CH2:19]O)[NH:11][C:10]1=[O:21])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.C1(C)C=C[C:32]([S:35]([O-])(=O)=O)=[CH:31]C=1.FC1C=CC=C[N+]=1C.S1C=CC=C1CC(O)=[O:55]>CC(C)=O.C1C=CC=CC=1>[C:32]([S:35][CH2:19][CH:12]1[NH:11][C:10](=[O:21])[CH:9]([CH2:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)(=[O:55])[CH3:31]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 8471Triethylamine2×HCID 159702-Thiopheneacetic acidHCID 1716312-Fluoro-1-methylpyridinium p-toluenesulfonateHCID 199308433-t-Butoxycarbonylmethyl-10-hydroxymethyl-2-oxo-1-azacyclodecane

Produkt 1

HCID 1993082910-(Acetylthiomethyl)-3-t-butoxycarbonylmethyl-2-oxo-1-azacyclodecane

Reagenzien, Katalysatoren, Lösungsmittel

2
HCID 180AcetoneLösungsmittelHCID 241BenzeneLösungsmittel

Versuchsvorschrift

3-t-Butoxycarbonylmethyl-10-hydroxymethyl-2-oxo-1-azacyclodecane (0.50 g, 1.67 mmol) is dissolved in acetone (5.0 mL) and benzene (5.0 mL). Triethylamine (0.26 mL, 1.9 mmol) is added, followed by 2-fluoro-1-methylpyridinium toluene-4-sulfonate (0.54 g, 1.9 mmol), and the reaction is stirred at room temperature for 90 minutes. Thiolacetic acid (0.14 mL, 1.9 mmol) and more triethylamine (0.26 mL, 1.9 mmol) are added, and the reaction is heated to reflux for 2 hours. The solvent is then removed, the crude product is partitioned between methylene chloride and water, and the aqueous phase is extracted several times with methylene chloride. The combined organic layers are dried (MgSO4) and the solvent is evaporated. The crude product is purified by silica gel chromatography (15% ethyl acetate/hexane) to give 10-(acetylthiomethyl)-3-t-butoxycarbonylmethyl-2-oxo-1-azacyclodecane, MS: M+1=358.

Aufarbeitung

  1. temperaturethe reaction is heated
  2. temperatureto reflux for 2 hours
  3. customThe solvent is then removed
  4. customthe crude product is partitioned between methylene chloride and water
  5. extractionthe aqueous phase is extracted several times with methylene chloride
  6. dry with materialThe combined organic layers are dried (MgSO4)
  7. customthe solvent is evaporated
  8. customThe crude product is purified by silica gel chromatography (15% ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-2d71b0967d484a04a693d8513b6e2d68
Quelldatensatz
uspto-grants-1995_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05426103

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