1,4-Bis(diphenylphosphino)butane → N-{(3S,7R,8R,9S)-8-(allyloxy)-7-benzyl-9-methyl-2,6-dioxo-1,5-dioxonan-3-yl}-3-(benzyloxy)-4-methoxypyridine-2-carboxamide

HRID 1071010Notes

Reaction equation

HRID 1071010 reaction equation
[CH3:1][CH:2](C)[C:3]([O:5][C@@H:6]1[C@@H:14]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:13](=[O:22])[O:12][CH2:11][C@H:10]([NH:23][C:24]([C:26]2[C:31]([O:32][CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)=[C:30]([O:40][CH3:41])[CH:29]=[CH:28][N:27]=2)=[O:25])[C:9](=[O:42])[O:8][C@H:7]1[CH3:43])=O.C1C=CC(P(C2C=CC=CC=2)CCCCP(C2C=CC=CC=2)C2C=CC=CC=2)=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].CCCCCC.CC(C)=O>[CH2:3]([O:5][C@H:6]1[C@H:7]([CH3:43])[O:8][C:9](=[O:42])[C@@H:10]([NH:23][C:24]([C:26]2[C:31]([O:32][CH2:33][C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=3)=[C:30]([O:40][CH3:41])[CH:29]=[CH:28][N:27]=2)=[O:25])[CH2:11][O:12][C:13](=[O:22])[C@@H:14]1[CH2:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[CH:2]=[CH2:1]

Participants

5

Reactant 2

HCID 821241,4-Bis(diphenylphosphino)butaneHCID 10282284HCID 10282284, compound

Product 1

HCID 69798673N-{(3S,7R,8R,9S)-8-(allyloxy)-7-benzyl-9-methyl-2,6-dioxo-1,5-dioxonan-3-yl}-3-(benzyloxy)-4-methoxypyridine-2-carboxamideYield 69%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 21880519Acetone hexaneSolvent

Procedure

Compound 7 was prepared in 69% yield using Compound 2 (65.2 g, 122.1 mmol) with dppb (5.20 g, 12.21 mmol), Pd2dba3 (2.79 g, 3.05 mmol) and ethyl methallylcarbonate (20.63 g, 158.73 mmol). Crude product upon chromatography on silica gel eluting with a mixture of hexane-acetone (1:1) afforded a white foam: m.p.=55-57° C., MS: (M+1)+=585, (M−1)+=583. Spectral data were consistent with the assigned structure.

Workup

  1. customafforded a white foam

Sources & evidence

ORD record
ord-88e9f4da74ed4ee5ba678af27847bcb7
Source dataset
uspto-grants-2005_06
Patent number
US06903219B2

Reaction notes

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