Toluene → Allyl 6beta-[(allyloxycarbonyl)acetamido]-2,2-dimethylpenam-3-carboxylate

HRID 128504

Reaktionsgleichung

Reaktionsgleichung von HRID 128504
[CH2:1]([O:4][C:5](=[O:10])[CH2:6][C:7]([OH:9])=O)[CH:2]=[CH2:3].[CH3:11][C:12]1([CH3:24])[S:16][C@@H:15]2[C@H:17]([NH2:20])[C:18](=[O:19])[N:14]2[C@H:13]1[C:21]([OH:23])=[O:22].[C:25]1(C)[CH:30]=CC=C[CH:26]=1>C(Cl)(Cl)Cl>[CH2:1]([O:4][C:5]([CH2:6][C:7]([NH:20][C@@H:17]1[C:18](=[O:19])[N:14]2[CH:13]([C:21]([O:23][CH2:30][CH:25]=[CH2:26])=[O:22])[C:12]([CH3:24])([CH3:11])[S:16][C@H:15]12)=[O:9])=[O:10])[CH:2]=[CH2:3]

Komponenten

5

Edukt 3

HCID 1140TolueneHCID 110826-Aminopenicillanic acidHCID 10888030Malonic acid monoallyl ester

Produkt 1

HCID 67785403Allyl 6beta-[(allyloxycarbonyl)acetamido]-2,2-dimethylpenam-3-carboxylateAusbeute 46 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

In a manner similar to that described for Example 1, method A, the title compound (3.53 g, 46%) was prepared from malonic acid monoallyl ester (2.88 g, 20 mmol) and 6-aminopenicillanic acid (4.33 g, 20 mmol) as colorless crystals: m.p. 59°-60° C. (toluene); IR (CHCl3) 1790, 1730, 1685 cm-1; 1 H NMR (CDCl3) δ 1.51 and 1.67 (each 3H, s, C2 -(CH3)2), 3.35-3.47 (2H, m, COCH2CO), 4.48 (1H, s, C3 -H), 4.60-4.70 (4H, m, 2xOCH2CH=CH2), 5.22-5.42 (4H, m, 2xOCH2CH=CH2), 5.56 (1H, d, J=4Hz, C5-H), 5.75 (1H, dd, J=4 and 9Hz, C6 -H), 5.84-6.00 (2H, m, 2xOCH2CH=CH2), 8.03 (1H, d, J=9Hz, NH).

Quellen und Nachweise

ORD-Eintrag
ord-67b89f0dcdb347d2ad2f4ceb4b51d66d
Quelldatensatz
uspto-grants-1995_11
Patentnummer
US05464616

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