Pyridine → 1-(1-Chloro-1-methoxycarbonylmethyl)-3-(triphenylmethylamino)-4-(3-phenylprop-2-ynylthio)azetidin-2-one

HRID 1578894

Reaktionsgleichung

Reaktionsgleichung von HRID 1578894
O[CH:2]([N:7]1[CH:10]([S:11][CH2:12][C:13]#[C:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:9]([NH:21][C:22]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:8]1=[O:41])[C:3]([O:5][CH3:6])=[O:4].N1C=CC=CC=1.S(Cl)([Cl:50])=O>O1CCCC1.O1CCOCC1>[Cl:50][CH:2]([N:7]1[CH:10]([S:11][CH2:12][C:13]#[C:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:9]([NH:21][C:22]([C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:8]1=[O:41])[C:3]([O:5][CH3:6])=[O:4]

Komponenten

6

Edukt 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 537149641-(1-Hydroxy-1-methoxycarbonylmethyl)-3-(triphenyl methylamino)-4-(3-phenylprop-2-ynylthio)azetidin-2-one

Produkt 1

HCID 215176541-(1-Chloro-1-methoxycarbonylmethyl)-3-(triphenylmethylamino)-4-(3-phenylprop-2-ynylthio)azetidin-2-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 312751,4-DioxaneLösungsmittel3×

Versuchsvorschrift

1-(1-Hydroxy-1-methoxycarbonylmethyl)-3-(triphenylmethylamino)-4-(3-phenylprop-2-ynylthio)azetidin-2-one (395mg) was dissolved in a 1:1 mixture of dry tetrahydrofuran and dioxan (14ml) and the solution, under nitrogen, was cooled to -10°. Pyridine (176mg) in dry dioxan (1ml) was then added, followed by the dropwise addition of thionyl chloride (0.153ml) in dry dioxan (4ml) over 2-3 minutes. After a further 15 minutes the precipitated solid was filtered off and the filtrate evaporated to dryness. Dry toluene was added and was decanted from any solid. The organic solution was evaporated to give 1-(1-Chloro-1-methoxycarbonylmethyl)-3-(triphenylmethylamino)-4-(3-phenylprop-2-ynylthio)azetidin-2-one as an amorphous solid (419mg), after drying overnight in vacuo. νmax (CHCl3) 1770 (broad, β-lactam and ester) cm-1.

Aufarbeitung

  1. temperaturethe solution, under nitrogen, was cooled to -10°
  2. filtrationAfter a further 15 minutes the precipitated solid was filtered off
  3. customthe filtrate evaporated to dryness
  4. additionDry toluene was added
  5. customwas decanted from any solid
  6. customThe organic solution was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-6117709153c1415b8fddf0072f08172f
Quelldatensatz
uspto-grants-1976_02
Patentnummer
US03939157

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