Ethyl Acetate → 6-(3-hydroxypropyl)-6-isopropyl-3-((S)-1-(4-(1-methyl-2-oxo-1,2-dihydropyridin-4-yl)phenyl)ethyl)-1,3-oxazinan-2-one

HRID 1640763Notes

Reaction equation

HRID 1640763 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][C:5]1([CH:29]([CH3:31])[CH3:30])[O:10][C:9](=[O:11])[N:8]([C@H:12]([C:14]2[CH:19]=[CH:18][C:17](B3OC(C)(C)C(C)(C)O3)=[CH:16][CH:15]=2)[CH3:13])[CH2:7][CH2:6]1.I[C:33]1[CH:38]=[CH:37][N:36]([CH3:39])[C:35](=[O:40])[CH:34]=1.C([O-])([O-])=O.[Cs+].[Cs+].CCOC(C)=O>O1CCOCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O>[OH:1][CH2:2][CH2:3][CH2:4][C:5]1([CH:29]([CH3:31])[CH3:30])[O:10][C:9](=[O:11])[N:8]([C@H:12]([C:14]2[CH:15]=[CH:16][C:17]([C:33]3[CH:38]=[CH:37][N:36]([CH3:39])[C:35](=[O:40])[CH:34]=3)=[CH:18][CH:19]=2)[CH3:13])[CH2:7][CH2:6]1

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 534080094-Iodo-1-methylpyridin-2(1H)-oneHCID 596357376-(3-hydroxypropyl)-6-isopropyl-3-((S)-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethyl)-1,3-oxazinan-2-one

Product 1

HCID 667357286-(3-hydroxypropyl)-6-isopropyl-3-((S)-1-(4-(1-methyl-2-oxo-1,2-dihydropyridin-4-yl)phenyl)ethyl)-1,3-oxazinan-2-one

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 6-(3-hydroxypropyl)-6-isopropyl-3-((S)-1-(4-(4,4,5,5-tetramethyl -1,3,2-dioxaborolan-2-yl)phenyl)ethyl)-1,3-oxazinan-2-one (40 mg, 0.092 mmol), 4-iodo-1-methylpyridin-2(1H)-one (20 mg, 0.085 mmol), Pd(PPh3)2Cl2 (6 mg, 0.0085 mmol), and Cs2CO3 (2 N, 0.425 mL, 0.85 mmol) in 1,4-dioxane (2 mL) was refluxed for 3 h under N2. The reaction mixture was treated with EtOAc (20 mL) and water (20 mL), and the organic layer was dried and concentrated in vacuo. The residue was purified by preparative HPLC to give two isomers.

Workup

  1. temperaturewas refluxed for 3 h under N2
  2. customthe organic layer was dried
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by preparative HPLC
  5. customto give two isomers

Sources & evidence

ORD record
ord-9756faf1df9240089ad1aa7b78dd3f27
Source dataset
uspto-grants-2012_02
Patent number
US08114868B2

Reaction notes

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