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 1071011Notes

Reaction equation

HRID 1071011 reaction equation
[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]

Participants

4

Reactant 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

Product 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 acetateYield 68%

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-3f1afc5605e34e63adaf46e0a03ecde4
Source dataset
uspto-grants-2005_06
Patent number
US06903219B2

Reaction notes

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