Hydrochloric Acid → (4S)-2,8-Dimethyl-4-[(toluenesulfonyl)amino]-5-nonanone

HRID 1110989

Reaktionsgleichung

Reaktionsgleichung von HRID 1110989
[NH:1]([S:10]([C:13]1[CH:19]=[CH:18][C:16](C)=[CH:15][CH:14]=1)(=[O:12])=[O:11])[C@H:2]([C:7]([OH:9])=O)[CH2:3][CH:4]([CH3:6])[CH3:5].[CH2:20]([Li])CCC.[CH2:25]([Mg]Br)[CH2:26][CH:27]([CH3:29])[CH3:28].Cl>C1COCC1.CCCCCC>[CH3:6][CH:4]([CH2:3][C@H:2]([NH:1][S:10]([C:13]1[C:14]([CH3:20])=[CH:15][CH:16]=[CH:18][CH:19]=1)(=[O:11])=[O:12])[C:7](=[O:9])[CH2:25][CH2:26][CH:27]([CH3:29])[CH3:28])[CH3:5]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 768170(2S)-4-methyl-2-(4-methylbenzenesulfonamido)pentanoic acidHCID 178418339ButyllithiumHCID 178418529HCID 178418529, Verbindung

Produkt 1

HCID 70040285(4S)-2,8-Dimethyl-4-[(toluenesulfonyl)amino]-5-nonanone

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 8058HexaneLösungsmittel

Versuchsvorschrift

To a stirred -78° C. solution of Ts-Leu (15 g, 53 mmol) in dry THF (240 ml) was added n-butyl lithium (57.8 ml of a 0.91M solution in hexane) followed 15 minutes later by isopentyl magnesium bromide (185 ml of a 0.8M solution in THF). The mixture was heated at reflux for 3 days, then cooled and poured into 0° C. 1M HCl (500 ml). The layers were separated and the aqueous phase was extracted with ether (3×150 ml). The combined organic layers were washed with saturated NaHCO3 (2×150 ml) and brine (150 ml). Drying and evaporating provided a residue which was chromatographed on silica gel to give 7.43 (41%) of the desired product. Mass spectrum: (M+H)+ =340.

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 3 days
  3. temperaturecooled
  4. additionpoured into 0° C
  5. customThe layers were separated
  6. extractionthe aqueous phase was extracted with ether (3×150 ml)
  7. washThe combined organic layers were washed with saturated NaHCO3 (2×150 ml) and brine (150 ml)
  8. customDrying
  9. customevaporating
  10. customprovided a residue which
  11. customwas chromatographed on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-ef198d439aab47da9912b3bb92489220
Quelldatensatz
uspto-grants-1990_12
Patentnummer
US04977277

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