4-Toluenesulfonyl chloride → HCID 59201488, Verbindung

HRID 451877Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 451877
[CH:1]1([O:7][C:8](=[O:29])[CH2:9][CH2:10][C@@H:11]([CH2:27][OH:28])[CH2:12][C@H:13]2[CH2:17][O:16][C:15]([CH3:19])([CH3:18])[N:14]2[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[S:30](Cl)([C:33]1[CH:39]=[CH:38][C:36]([CH3:37])=[CH:35][CH:34]=1)(=[O:32])=[O:31]>CN(C1C=CN=CC=1)C.N1C=CC=CC=1>[CH:1]1([O:7][C:8](=[O:29])[CH2:9][CH2:10][C@@H:11]([CH2:27][O:28][S:30]([C:33]2[CH:39]=[CH:38][C:36]([CH3:37])=[CH:35][CH:34]=2)(=[O:32])=[O:31])[CH2:12][C@H:13]2[CH2:17][O:16][C:15]([CH3:18])([CH3:19])[N:14]2[C:20]([O:22][C:23]([CH3:24])([CH3:26])[CH3:25])=[O:21])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Komponenten

5

Edukt 2

HCID 73974-Toluenesulfonyl chlorideHCID 59201656HCID 59201656, Verbindung

Produkt 1

HCID 59201488HCID 59201488, VerbindungAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 1049PyridineLösungsmittel

Versuchsvorschrift

The (S)-tert-butyl 4-((R)-5-(cyclohexyloxy)-2-(hydroxymethyl)-5-oxopentyl)-2,2-dimethyloxazolidine-3-carboxylate (4.97 g, 12.0 mmol, 1.0 equiv), DMAP (1.47 mg, 12.0 mmol, 1.0 equiv) and tosyl chloride (9.2 g, 48.2 mmol, 4.0 equiv) were dissolved in pyridine (100 mL) and the solution stirred for 18 hr. The pyridine was removed in vacuo and the residue taken up in EtOAc/0.5 M HCl. The layers were separated, and the organic layer washed with 10% K2CO3, brine, dried over Na2SO4, filtered and evaporated. The tosylate was purified by flash chromatography on silica, (12 g), eluting with 0-29% EtOAc in hexanes. This afforded 6.66 g (98% yield) of (S)-tert-butyl 4-((R)-5-(cyclohexyloxy)-5-oxo-2-(tosyloxymethyl)pentyl)-2,2-dimethyloxazolidine-3-carboxylate as a white solid. MS ESI +ve m/z 590 (M+Na).

Aufarbeitung

  1. customThe pyridine was removed in vacuo
  2. customThe layers were separated
  3. washthe organic layer washed with 10% K2CO3, brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe tosylate was purified by flash chromatography on silica, (12 g)
  8. washeluting with 0-29% EtOAc in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-994473be16c544929eeb5664b8a77695
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08487108B2

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