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Tris(furan-2-yl)phosphane → HCID 14167873, Verbindung

HRID 1608371
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1608371
[C:1]1([CH2:7][C:8]([NH:10][CH:11]2[C:42](=[O:43])[N:13]3[C:14]([C:26]([O:28][CH:29]([C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)[C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)=[O:27])=[C:15](OS(C(F)(F)F)(=O)=O)[CH2:16][S:17][C@H:12]23)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:44][O:45][C:46]1[CH:51]=[CH:50][C:49]([Sn](CCCC)(CCCC)CCCC)=[CH:48][CH:47]=1.O1C=CC=C1P(C1OC=CC=1)C1OC=CC=1>CN1CCCC1=O.C(OCC)(=O)C.[Cl-].[Zn+2].[Cl-].C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.[Pd]>[C:1]1([CH2:7][C:8]([NH:10][CH:11]2[C:42](=[O:43])[N:13]3[C:14]([C:26]([O:28][CH:29]([C:30]4[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=4)[C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)=[O:27])=[C:15]([C:49]4[CH:50]=[CH:51][C:46]([O:45][CH3:44])=[CH:47][CH:48]=4)[CH2:16][S:17][C@H:12]23)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 3

HCID 521585Tris(furan-2-yl)phosphaneHCID 2762547TRIBUTYL(4-METHOXYPHENYL)STANNANEHCID 14167862HCID 14167862, Verbindung

Produkt 1

HCID 14167873HCID 14167873, VerbindungAusbeute 57 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 154270
1,5-Diphenylpenta-1,4-dien-3-one;palladium
Katalysator
HCID 3007855ZincchlorideKatalysator
HCID 8857Ethyl AcetateLösungsmittel
HCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Versuchsvorschrift

A mixture of 0.1029 g ((0.000163 mole) of diphenylmethyl 7-phenylacetamido-3-(trifluoromethylsulfonyloxy)-3-cephem- -4-carboxylate, 0.0775 g (0.000195 mole) of (p-methoxyphenyl)tri-n-butylstannane, 0.044 g (0.00032 mole) of zinc chloride and 0.00378 g (0.000016 mole) of tri(2-furyl)-phosphine in 4 mL of dry 1-methyl-2-pyrrolidinone, under an argon atmosphere, was degassed for 30 seconds. Then 0.0047 g (0.000008 mole) of palladium(0) bis(dibenzylidene acetone) was added all at once. The reaction mix was stirred at 50° for 5.5 hrs and room temperature for 16 hrs. The reaction mix was then diluted with ethyl acetate and the organic solution washed with dilute ammonium chloride. The ethyl acetate was removed at reduced pressure and replaced with acetonitrile. The organic phase was washed with n-pentane and the acetonitrile removed at reduced pressure. The residue was chromatographed on silica gel to yield 0.0548 g (57%) of diphenylmethyl 7-phenylacetamido-3-(p-methoxyphenyl)-3cephem-4-carboxylate. The nuclear magnetic resonance spectrum was consistent for the desired structure.

Aufarbeitung

  1. customunder an argon atmosphere, was degassed for 30 seconds
  2. additionThe reaction mix
  3. additionThe reaction mix
  4. washthe organic solution washed with dilute ammonium chloride
  5. customThe ethyl acetate was removed at reduced pressure
  6. washThe organic phase was washed with n-pentane
  7. customthe acetonitrile removed at reduced pressure
  8. customThe residue was chromatographed on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-c3b842485f144005991ce157d4e260cc
Quelldatensatz
uspto-grants-1989_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04870168

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