HCID 1501988, compound → HCID 59749467, compound

HRID 747222Notes

Reaction equation

HRID 747222 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:12]2[CH2:16][CH:15]([CH2:17][NH:18][C:19](=[O:21])[CH3:20])[O:14][N:13]=2)[CH:5]=[CH:6][C:7]=1[Sn](C)(C)C.[OH:22][CH2:23][C@H:24]1[O:28][C:27](=[O:29])[N:26]([C:30]2[CH:35]=[CH:34][C:33](I)=[CH:32][CH:31]=2)[CH2:25]1>O1CCOCC1.CS(C)=O>[F:1][C:2]1[CH:3]=[C:4]([C:12]2[CH2:16][CH:15]([CH2:17][NH:18][C:19](=[O:21])[CH3:20])[O:14][N:13]=2)[CH:5]=[CH:6][C:7]=1[C:33]1[CH:32]=[CH:31][C:30]([N:26]2[CH2:25][C@H:24]([CH2:23][OH:22])[O:28][C:27]2=[O:29])=[CH:35][CH:34]=1

Participants

5

Reactant 2

HCID 1501988HCID 1501988, compoundHCID 59749521HCID 59749521, compound

Product 1

HCID 59749467HCID 59749467, compoundYield 0.9%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

N-({3-[3-Fluoro-4-(trimethylstannyl)phenyl]-4,5-dihydroisoxazol-5-yl]methyl}acetamide (600 mg, 1.5 mmol), (5S)-5-(hydroxymethyl)-3-(4-iodophenyl)-1,3-oxazolidin-2-one (319 mg, 1.0 mmol) and 2-trifurylphosphine (23 mg, 0.1 mmol) were dissolved in dry 1,4-dioxane (10 ml) and the reaction mixture placed under an atmosphere of argon. Tris(dibenzylidineacetone)dipalladium (0) chloroform adduct (52 mg, 0.05 mmol) was added and the reaction mixture stirred for 16 hours at 90° C. Silica gel (0.5 g) was added and the mixture concentrated in vacuo. Purification by column chromatography (10 g silica gel bond elut: 0% to 5% methanoydichloromethane) yielded an off white solid. This was dissolved in dimethylsulphoxide (0.5 ml) and purified by reverse phase preparative HPLC using a gradient from 20% acetonitrile/water to 70% acetonitrile/water to give 3.7 mg of the desired compound.

Workup

  1. additionSilica gel (0.5 g) was added
  2. concentrationthe mixture concentrated in vacuo
  3. customPurification by column chromatography (10 g silica gel bond elut: 0% to 5% methanoydichloromethane)
  4. customyielded an off white solid
  5. custompurified by reverse phase preparative HPLC

Sources & evidence

ORD record
ord-ac9261f4b696418ca3b252771336a033
Source dataset
uspto-grants-2008_07
Patent number
US07396847B2

Reaction notes

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