Bromide ion → Methyl 2-((tert-butoxycarbonyl)amino)pent-4-enoate

HRID 1377422Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1377422
C(O[CH:5]([NH:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[C:6]([O:8][CH3:9])=[O:7])(=O)C.[CH2:18](Br)[CH:19]=[CH2:20].[Br-]>CN(C=O)C.[Zn]>[CH3:9][O:8][C:6](=[O:7])[CH:5]([NH:10][C:11]([O:13][C:14]([CH3:15])([CH3:16])[CH3:17])=[O:12])[CH2:20][CH:19]=[CH2:18]

Komponenten

6

Edukt 3

HCID 259Bromide ionHCID 7841Allyl bromideHCID 10922855Acetyloxy[[(1,1-dimethylethoxy)carbonyl]amino]acetic acid methyl ester

Produkt 1

HCID 10857232Methyl 2-((tert-butoxycarbonyl)amino)pent-4-enoateAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23994ZincKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To an ice cooled suspension of the product of Example 2 (0.525 mg, 2.12 mmol) and zinc dust (278 mg, 4.25 mmol) in DMF (4 mL) under nitrogen was added slowly via syringe neat allyl bromide (514 mg, 4.25 mmol). The bromide was added at such a rate as to maintain the internal temperature between 20° and 25° C., then stirred at that temperature for an additional 1 hour. Extractive workup and silica gel chromatography as described in Example 3 afforded 486 mg (100%) of product as a colorless oil.

Aufarbeitung

  1. temperatureto maintain the internal temperature between 20° and 25° C.

Quellen und Nachweise

ORD-Eintrag
ord-0569477272214ed39164694a4b9eff7c
Quelldatensatz
uspto-grants-1997_09
Patentnummer
US05665598

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