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Sodium Thiosulfate → methyl (2S)-2-{[N-(tert-butoxycarbonyl)-L-alanyl]amino}-3-oxobutanoate

HRID 869727
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 869727
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:11]([NH:13][C@H:14]([C:18]([O:20][CH3:21])=[O:19])[C@@H:15]([CH3:17])[OH:16])=[O:12])[CH3:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.S([O-])([O-])(=O)=S.[Na+].[Na+].C(=O)(O)[O-].[Na+]>ClCCl>[C:1]([O:5][C:6]([NH:8][C@H:9]([C:11]([NH:13][C@@H:14]([C:15](=[O:16])[CH3:17])[C:18]([O:20][CH3:21])=[O:19])=[O:12])[CH3:10])=[O:7])([CH3:3])([CH3:2])[CH3:4]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 11483528methyl N-(tert-butoxycarbonyl)-L-alanyl-L-threoninate

Produkt 1

HCID 86674523methyl (2S)-2-{[N-(tert-butoxycarbonyl)-L-alanyl]amino}-3-oxobutanoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of methyl N-(tert-butoxycarbonyl)-L-alanyl-L-threoninate (9.00 g, 29.6 mmol) in dichloromethane (90 mL) was added Dess-Martin periodinane (15.1 g, 35.5 mmol) at room temperature. After being stirred for 70 min, saturated aqueous sodium thiosulfate solution was added, then the reaction mixture was stirred for 15 min. The mixture was poured into saturated aqueous sodium bicarbonate, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over sodium sulfate, filtrated and concentrated in vacuo. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1 to 1:1) to give methyl (2S)-2-{[N-(tert-butoxycarbonyl)-L-alanyl]amino}-3-oxobutanoate. MS (APCI): m/z 303 (M+H).

Aufarbeitung

  1. stirringthe reaction mixture was stirred for 15 min
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltrated
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1 to 1:1)

Quellen und Nachweise

ORD-Eintrag
ord-2b6f12c30d794535bc581ed5f5fa7e7e
Quelldatensatz
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08969376B2

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