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

HRID 1283329

Reaktionsgleichung

Reaktionsgleichung von HRID 1283329
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.

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-78df11b30b904bb3b8837a11797bb2c7
Quelldatensatz
uspto-grants-1976_08
Patentnummer
US03974154

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