Dichloromethane → (S)-2-methylpropane-2-sulfinamide tert-butyl(dimethyl){[(1S,2R,5E)-2-methyl-6-(4-nitrophenyl)-1-(phenoxymethyl)hex-5-en-1-yl]oxy}silane

HRID 1916824

Reaktionsgleichung

Reaktionsgleichung von HRID 1916824
[Si:1]([O:8][C@@H:9]([C@H:18]([NH:23][S:24]([C:26]([CH3:29])([CH3:28])[CH3:27])=[O:25])[CH2:19][CH2:20]C=C)[CH2:10][O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[N+:30]([C:33]1[CH:40]=[CH:39][C:36]([CH:37]=[CH2:38])=[CH:35][CH:34]=1)([O-:32])=[O:31].[CH2:41](Cl)Cl>>[CH3:27][C:26]([S@@:24]([NH2:23])=[O:25])([CH3:29])[CH3:28].[C:4]([Si:1]([CH3:2])([CH3:3])[O:8][C@H:9]([CH2:10][O:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[C@H:18]([CH3:41])[CH2:19][CH2:20]/[CH:38]=[CH:37]/[C:36]1[CH:39]=[CH:40][C:33]([N+:30]([O-:32])=[O:31])=[CH:34][CH:35]=1)([CH3:5])([CH3:6])[CH3:7]

Komponenten

4

Edukt 3

HCID 6344DichloromethaneHCID 74811-Ethenyl-4-nitrobenzeneHCID 66776706N-[(1R)-1-((1S)-1-{[tert-butyl(dimethyl)silyl]oxy}-2-phenoxyethyl)pent-4-en-1-yl]-2-methylpropane-2-sulfinamide

Produkt 1

HCID 66777039(S)-2-methylpropane-2-sulfinamide tert-butyl(dimethyl){[(1S,2R,5E)-2-methyl-6-(4-nitrophenyl)-1-(phenoxymethyl)hex-5-en-1-yl]oxy}silane

Reaktionsbedingungen

Temperatur
35 °C

Versuchsvorschrift

The major product alkene, N-[(1R)-1-((1S)-1-{[tert-butyl(dimethyl)silyl]oxy}-2-phenoxyethyl)pent-4-en-1-yl]-2-methylpropane-2-sulfinamide (160 mg; 0.364 mmol) from Step F, 4-nitrostyrene (220 mg; 1.475 mmol) and Grubbs-II metathesis catalyst (45 mg; 0.053 mmol) were combined in anhydrous methylene chloride (6 ml) and the resulting reaction mixture stirred for 20 hours at 35° C. The crude product solution was concentrated under reduced pressure and the residues purified by silica gel plate chromatography on (20 cm×20 cm×1000 microns) eluted with hexanes and ethyl acetate (2:1 v/v) from which 116 mg of the desired metathesis product was obtained, m/z (ES) 561.22 (M+H)+.

Aufarbeitung

  1. customthe resulting reaction mixture
  2. concentrationThe crude product solution was concentrated under reduced pressure
  3. customthe residues purified by silica gel plate chromatography on (20 cm×20 cm×1000 microns)
  4. washeluted with hexanes and ethyl acetate (2:1 v/v) from which 116 mg of the desired metathesis product
  5. customwas obtained

Quellen und Nachweise

ORD-Eintrag
ord-1d41f4c907fc422f83d7a0c8867ec7b5
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08618144B2

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