Sodium Hydroxide → Tert-butyl [2-(benzylthio)-3,3-dimethoxypropyl]carbamate

HRID 504800Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 504800
[CH2:1]([S:8][CH:9]([CH:12]([O:15][CH3:16])[O:13][CH3:14])[CH2:10][NH2:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].[C:19](=O)([OH:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22]>O1CCCC1>[CH2:1]([S:8][CH:9]([CH:12]([O:13][CH3:14])[O:15][CH3:16])[CH2:10][NH:11][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 14798Sodium HydroxideHCID 3015642Mono-tert-butyl carbonateHCID 574759902-(Benzylthio)-3,3-dimethoxypropan-1-amine

Produkt 1

HCID 59136115Tert-butyl [2-(benzylthio)-3,3-dimethoxypropyl]carbamateAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

2-(Benzylthio)-3,3-dimethoxypropan-1-amine (1 g) was dissolved in tetrahydrofuran (7 mL), and 1N aqueous sodium hydroxide solution (10 mL) was added. A solution of t-butyl bicarbonate (993 mg) in tetrahydrofuran (3 mL) was added dropwise to the reaction solution under ice-cooling, and the mixture was stirred overnight at room temperature. The reaction mixture was extracted with ethyl acetate, and the organic layer was washed with saturated brine, and dried over sodium sulfate. The obtained solution was filtrated through basic silica gel, and concentrated to give the title compound (1.39 g, yield 99%) as a pale-yellow oil.

Aufarbeitung

  1. temperaturecooling
  2. extractionThe reaction mixture was extracted with ethyl acetate
  3. washthe organic layer was washed with saturated brine
  4. dry with materialdried over sodium sulfate
  5. filtrationThe obtained solution was filtrated through basic silica gel
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-8a9dd7db50624ace86a29cfcc7553e35
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07777047B2

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