1,4-Bis(diphenylphosphino)butane → ({2-[({(3s,7r,8r,9s)-8-(Allyloxy)-7-benzyl-9-methyl-2,6-dioxo-1,5-dioxonan-3-yl}amino)carbonyl]-4-methoxypyridine-3-yl}oxy)methyl acetate

HRID 1071011Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1071011
[C:1]([O:4][CH2:5][O:6][C:7]1[C:8]([C:15]([NH:17][C@H:18]2[CH2:26][O:25][C:24](=[O:27])[C@H:23]([CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C@@H:22]([OH:35])[C@H:21]([CH3:36])[O:20][C:19]2=[O:37])=[O:16])=[N:9][CH:10]=[CH:11][C:12]=1[O:13][CH3:14])(=[O:3])[CH3:2].[CH:38]1[CH:43]=CC(P(C2C=CC=CC=2)CCCCP(C2C=CC=CC=2)C2C=CC=CC=2)=C[CH:39]=1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:1]([O:4][CH2:5][O:6][C:7]1[C:8]([C:15]([NH:17][C@H:18]2[CH2:26][O:25][C:24](=[O:27])[C@H:23]([CH2:28][C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)[C@@H:22]([O:35][CH2:43][CH:38]=[CH2:39])[C@H:21]([CH3:36])[O:20][C:19]2=[O:37])=[O:16])=[N:9][CH:10]=[CH:11][C:12]=1[O:13][CH3:14])(=[O:3])[CH3:2]

Komponenten

4

Edukt 2

HCID 821241,4-Bis(diphenylphosphino)butaneHCID 69801412({2-[({(3S,7R,8R,9S)-7-benzyl-8-(hydroxy)-9-methyl-2,6-dioxo-1,5-dioxonan-3-yl}amino)carbonyl]-4-methoxypyridine-3-yl}oxy)methyl acetate

Produkt 1

HCID 59989566({2-[({(3s,7r,8r,9s)-8-(Allyloxy)-7-benzyl-9-methyl-2,6-dioxo-1,5-dioxonan-3-yl}amino)carbonyl]-4-methoxypyridine-3-yl}oxy)methyl acetateAusbeute 68 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysator

Versuchsvorschrift

Compound 8 was prepared in 68% yield using Compound 3 (150 mg, 0.29 mmol) with dppb (12 mg, 0.03 mmol), Pd2dba3 (5.30 mg, 0.006 mmol) and ethyl methallylcarbonate (41 mg, 0.31 mmol). Purification by flash column chromatography on silica gel eluting with a mixture of hexane-acetone (1:1) gave a white foam: MS: (M+1)+=557, (M−1)+=555. Spectral data were consistent with the assigned structure.

Aufarbeitung

  1. customPurification by flash column chromatography on silica gel eluting
  2. additionwith a mixture of hexane-acetone (1:1)
  3. customgave a white foam

Quellen und Nachweise

ORD-Eintrag
ord-3f1afc5605e34e63adaf46e0a03ecde4
Quelldatensatz
uspto-grants-2005_06
Patentnummer
US06903219B2

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