Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → Benzhydryl (E)-(2S,3S,5R)-3-(2-ethoxycarbonyl-vinyl)-3-methyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate

HRID 263742Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 263742
[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:30][C:31]([CH:33]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:32])[CH3:29]>C1COCC1>[CH2:28]([O:30][C:31](/[CH:33]=[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:32])[CH3:29]

Komponenten

4

Edukt 2

HCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 10762402benzhydryl (2S,3R,5R)-3-formyl-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

Produkt 1

HCID 10766016Benzhydryl (E)-(2S,3S,5R)-3-(2-ethoxycarbonyl-vinyl)-3-methyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

500 mg (1.30 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 20 ml of THF under argon and treated with 500 mg (1.40 mmol) of ethoxycarbonylmethylene-triphenylphosphorane. The yellow solution was stirred at 50° C. for 75 minutes and subsequently concentrated. The residue remaining behind was chromatographed over silica gel (0.040-0.063 mm particle size) with ethyl acetate:hexane (9:16) as the eluent. Yield: 520 mg (88%) of yellow-orange resin; IR (film): 1783, 1747, 1717, 1650 cm-1MS: (M--CONH) 406, (M--CHPh2) 284 1H-NMR (250MHz, CDCl3): δ[ppm]=1.31(t,3H,J=7Hz),1.34(s,3H), 3.13(dd,1H,J=2Hz, 16Hz,6-H), 3.57(dd,1H,J=4Hz, 16Hz,6-H), 4.22(q,2H,J=7Hz), 4.78(s,1H,2-H), 5.30(dd,1H,J=4.2Hz, 5-H), 5.97(d,1H,J=15Hz,=CH), 6.94(s,1H,CHPh2), 7.07(d,1H,J=15Hz,=CH), 7.30-7.38(m,10H,Ph).

Aufarbeitung

  1. concentrationsubsequently concentrated
  2. customThe residue remaining behind was chromatographed over silica gel (0.040-0.063 mm particle size) with ethyl acetate:hexane (9:16) as the eluent

Quellen und Nachweise

ORD-Eintrag
ord-7ea561ad4d8c4008b5e085fa9f1f2ab7
Quelldatensatz
uspto-grants-1997_07
Patentnummer
US05644053

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