Benzyl 2-(triphenyl-lambda5-phosphanylidene)acetate → HCID 86750936, Verbindung

HRID 263743Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 263743
[CH:1]([C@:3]1([CH3:27])[S:9][C@H:8]2[N:5]([C:6](=[O:10])[CH2:7]2)[C@H:4]1[C:11]([O:13][CH:14]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])=O.[CH2:28]([O:35][C:36]([CH:38]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:37])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>C1COCC1>[CH2:28]([O:35][C:36](/[CH:38]=[CH:1]/[C@:3]1([CH3:27])[S:9][C@H:8]2[N:5]([C:6](=[O:10])[CH2:7]2)[C@H:4]1[C:11]([O:13][CH:14]([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)=[O:12])=[O:37])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Komponenten

4

Edukt 2

HCID 3862746Benzyl 2-(triphenyl-lambda5-phosphanylidene)acetateHCID 10762402HCID 10762402, Verbindung

Produkt 1

HCID 86750936HCID 86750936, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

763 mg (2.0 mmol) of benzhydryl (2S,3R,5R)-3-formyl-3-methyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate were dissolved in 15 ml of THF under argon, treated with 821 mg (2.0 mmol) of benzyloxycarbonylmethylene-triphenylphosphorane and the orange solution was stirred at 50° C. for 2 hours. It was left to cool to room temperature, the solvent was removed on a rotary evaporator and the red-brown oil was chromatographed over silica gel (particle size 0.040-0.063 mm) with ethyl acetate:hexane (9:16) as the eluent. Yield: 800 mg (78%) of orange foam IR (film): 1782, 1746, 1721, 1649, 985 cm-1MS: (M+H)+ 514.3 1H-NMR- (250MHz, CDCl3): δ[ppm]=1.33(s,3H), 3.11 (dd,1H,J=16Hz, 1.6Hz, 6-H), 3.56(dd,1H,J=16Hz, 4.2Hz, 6-H), 4.78(s,1H,2-H), 5.20(s,2H), 5.36(dd,1H, J=1.6Hz, 4.2Hz, 5-H), 6.01(d,1H,J=15Hz,=CH), 6.93(s,1H,CHPh2), 7.12(d,1H,J=15Hz, =CH), 7.30-7.43(m,15H,Ph).

Aufarbeitung

  1. waitIt was left
  2. temperatureto cool to room temperature
  3. customthe solvent was removed on a rotary evaporator
  4. customthe red-brown oil was chromatographed over silica gel (particle size 0.040-0.063 mm) with ethyl acetate:hexane (9:16) as the eluent

Quellen und Nachweise

ORD-Eintrag
ord-cc259c0f07b94c51975a2a4fed50a4e7
Quelldatensatz
uspto-grants-1997_07
Patentnummer
US05644053

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