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Water → tert-butyl (4R)-4-{[(benzyloxy)carbonyl]amino}pentanoate

HRID 1374415
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1374415
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([CH2:22]Br)[CH2:13][CH2:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([SnH](CCCC)CCCC)CCC.N(C(C)(C)C#N)=NC(C)(C)C#N.O>C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]([NH:11][C@H:12]([CH3:22])[CH2:13][CH2:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 962WaterHCID 5948TributylstannaneHCID 6547AzobisisobutyronitrileHCID 69349527HCID 69349527, Verbindung

Produkt 1

HCID 11109586tert-butyl (4R)-4-{[(benzyloxy)carbonyl]amino}pentanoateAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140
Toluene
Lösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of tert-butyl(4S)-4-{[(benzyloxy)carbonyl]amino}-5-bromopentanoate (4.5 g, 11.7 mmol) and tributyltin hydride (6.3 ml, 23.4 mmol) in toluene (45 ml) was added 2,2′-azobisisobutyronitrile (0.19 g, 1.2 mmol) and the mixture was stirred at 80° C. for 20 minutes. To the reaction mixture was added water, and the solution was extracted three times with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate and the organic solvent was removed under reduced pressure. The residue was purified with silica gel chromatography to give tert-butyl (4R)-4-{[(benzyloxy)carbonyl]amino}pentanoate (3.5 g, 98%).

Aufarbeitung

  1. extractionthe solution was extracted three times with ethyl acetate
  2. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe organic solvent was removed under reduced pressure
  5. customThe residue was purified with silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-bf3169adf428459bac42baf028eefd8b
Quelldatensatz
uspto-grants-2007_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07163936B2

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