Allyl chloroacetate → (3S-trans)-[[3-[(t-Butyloxycarbonyl)amino]-2-methyl-4-oxo-1-azetidinyl]oxy]acetic acid, 2-propenyl ester

HRID 2165284

Reaktionsgleichung

Reaktionsgleichung von HRID 2165284
[C:1]([O:5][C:6]([NH:8][C@H:9]1[C@H:12]([CH3:13])[N:11]([OH:14])[C:10]1=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl[CH2:17][C:18]([O:20][CH2:21][CH:22]=[CH2:23])=[O:19]>CN(C)C=O>[C:1]([O:5][C:6]([NH:8][C@@H:9]1[C:10](=[O:15])[N:11]([O:14][CH2:17][C:18]([O:20][CH2:21][CH:22]=[CH2:23])=[O:19])[C@H:12]1[CH3:13])=[O:7])([CH3:2])([CH3:4])[CH3:3]

Komponenten

4

Edukt 2

HCID 76206Allyl chloroacetateHCID 12946603tert-butyl N-[(2S,3S)-1-hydroxy-2-methyl-4-oxoazetidin-3-yl]carbamate

Produkt 1

HCID 57212832(3S-trans)-[[3-[(t-Butyloxycarbonyl)amino]-2-methyl-4-oxo-1-azetidinyl]oxy]acetic acid, 2-propenyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 17.3 g of (3S-trans)-3-(t-butyloxycarbonylamino)-1-hydroxy-4-methyl-2-azetidinone and 12.9 g of chloroacetic acid, 2-propenyl ester in 350 ml of dry dimethylformamide. The mixture was allowed to stand for 4 days at room temperature and subsequently worked up as described in Example 90B. Yield 25.5 g of crude ester.

Quellen und Nachweise

ORD-Eintrag
ord-38732c53d02e4c1f88f3a8f3f7fb6405
Quelldatensatz
uspto-grants-1990_07
Patentnummer
US04939253

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