({2-[({(3S,7R,8R,9S)-7-benzyl-9-methyl-8-[(2-methylprop-2-enyl)oxy]-2,6-dioxo-1,5-dioxonan-3-yl}amino)carbonyl]-4-methoxypyridine-3-yl}oxy)methyl acetate → {[2-({[(3S,7R,8R,9S)-7-benzyl-8-isobutoxy-9-methyl-2,6-dioxo-1,5-dioxonan-3-yl}amino)carbonyl]-4-methoxypyridine-3-yl}oxy)methyl acetate

HRID 1071012Notes

Reaction equation

HRID 1071012 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]([O:35][CH2:36][C:37]([CH3:39])=[CH2:38])[C@H:21]([CH3:40])[O:20][C:19]2=[O:41])=[O:16])=[N:9][CH:10]=[CH:11][C:12]=1[O:13][CH3:14])(=[O:3])[CH3:2].[H][H]>[Pd].C(OCC)(=O)C>[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][CH2:36][CH:37]([CH3:38])[CH3:39])[C@H:21]([CH3:40])[O:20][C:19]2=[O:41])=[O:16])=[N:9][CH:10]=[CH:11][C:12]=1[O:13][CH3:14])(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 59989553({2-[({(3S,7R,8R,9S)-7-benzyl-9-methyl-8-[(2-methylprop-2-enyl)oxy]-2,6-dioxo-1,5-dioxonan-3-yl}amino)carbonyl]-4-methoxypyridine-3-yl}oxy)methyl acetateHCID 178418361HCID 178418361, compound

Product 1

HCID 59989581{[2-({[(3S,7R,8R,9S)-7-benzyl-8-isobutoxy-9-methyl-2,6-dioxo-1,5-dioxonan-3-yl}amino)carbonyl]-4-methoxypyridine-3-yl}oxy)methyl acetateYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Compound 12 was prepared in 95% yield using Compound 6 (6.0 g, 10.5 mmol) with 10% palladium on charcoal (1.2 g) and hydrogen (40 psi) in ethyl acetate (150 mL) for 1.5 hour. Recrystallization from a mixture of hot methylcyclohexane and toluene (4:1) gave 5.7 g of white needles: m.p.134-136° C. Spectral data were consistent with the assigned structure.

Workup

  1. customfor 1.5 hour
  2. customRecrystallization
  3. additionfrom a mixture of hot methylcyclohexane and toluene (4:1)

Sources & evidence

ORD record
ord-d6168b821f794d7d803151779a3c1c72
Source dataset
uspto-grants-2005_06
Patent number
US06903219B2

Reaction notes

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