1,4-Dioxane → HCID 22494108, compound

HRID 1816605Notes

Reaction equation

HRID 1816605 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:11]=[C:12]([CH2:24][CH:25]([O:31][CH:32]([CH3:34])C)[C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH:13]=[CH:14][C:15]=1[O:16][S:17]([C:20]([F:23])([F:22])[F:21])(=[O:19])=[O:18])=[O:7])([CH3:4])([CH3:3])[CH3:2].C([Sn](CCCC)(CCCC)[C:40]1[O:41][CH:42]=[CH:43][CH:44]=1)CCC.[Cl-].[Li+].O1CCOC[CH2:56]1>>[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:11]=[C:12]([CH2:24][CH:25]([O:31][CH2:32][CH:34]([C:40]2[O:41][CH:42]=[CH:43][CH:44]=2)[CH3:56])[C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH:13]=[CH:14][C:15]=1[O:16][S:17]([C:20]([F:23])([F:22])[F:21])(=[O:19])=[O:18])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 4

HCID 312751,4-DioxaneHCID 433294Lithium ChlorideHCID 43936882-(Tributylstannyl)furanHCID 22494261HCID 22494261, compound

Product 1

HCID 22494108HCID 22494108, compound

Conditions

Temperature
80 °C

Procedure

334 mg of ethyl 3-(3-[(tertiary butoxycarbonyl)amino]methyl-4-[(trifluoromethyl)sulfonyl]oxyphenyl)-2-isopropoxypropionate was dissolved in 4 ml dioxane. 280 mg of 2-tributylstannylfuran, 75 mg of tetrakistriphenylphosphine palladium and 83 mg of lithium chloride were added thereto, followed by stirring overnight at 80° C. in a nitrogen atmosphere. The reaction mixture was concentrated and the residue was purified by silica gel column chromatography, to give 180 mg of ethyl 3-(3-[(tertiary butoxycarbonyl)amino]methyl-4-[(trifluoromethyl)sulfonyl]oxyphenyl)-2-(2-furyl)propoxypropionate from fractions eluted with hexane-ethyl acetate (7:1).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-f5362718a202461cb0d56957affe347a
Source dataset
uspto-grants-2005_04
Patent number
US06884821B1

Reaction notes

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