Potassium Phosphate, Tribasic → HCID 69119900, compound

HRID 2118336Notes

Reaction equation

HRID 2118336 reaction equation
[CH2:1]([O:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][N:12]1[CH2:16][C@@H:15]([C:17]2[CH:28]=[CH:27][C:20]3[O:21][C:22]([CH3:26])([CH3:25])[O:23][CH2:24][C:19]=3[CH:18]=2)[O:14][C:13]1=[O:29])[CH2:2][CH:3]=[CH2:4].C12BC(CCC1)CCC2.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[CH2:47]([CH:50]([S:54]([C:57]1[CH:62]=[CH:61][CH:60]=[C:59](Br)[CH:58]=1)(=[O:56])=[O:55])[CH2:51][CH:52]=[CH2:53])[CH:48]=[CH2:49]>C1COCC1.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:26][C:22]1([CH3:25])[O:21][C:20]2[CH:27]=[CH:28][C:17]([C@H:15]3[O:14][C:13](=[O:29])[N:12]([CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][O:5][CH2:1][CH2:2][CH2:3][CH2:4][C:61]4[CH:60]=[CH:59][CH:58]=[C:57]([S:54]([CH:50]([CH2:51][CH:52]=[CH2:53])[CH2:47][CH:48]=[CH2:49])(=[O:55])=[O:56])[CH:62]=4)[CH2:16]3)=[CH:18][C:19]=2[CH2:24][O:23]1

Participants

9

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 789669-Borabicyclo(3.3.1)nonaneHCID 69119699HCID 69119699, compoundHCID 69119906HCID 69119906, compound

Product 1

HCID 69119900HCID 69119900, compoundYield 75.8%

Reagents, catalysts & solvents 4

HCID 11776TriphenylphosphineCatalystHCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of (5R)-3-[6-(3-buten-1-yloxy)hexyl]-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-one (1.00 g) in THF (2 ml) was added a 0.5M solution of 9-borabicyclo[3.3.1]nonane (9-BBN) in THF (6 ml). The solution was stirred at room temperature under nitrogen for 2 h. Tripotassium phosphate (1.05 g) in water (1.5 ml) was added followed by 1-[(1-allylbut-3-enyl)sulfonyl]-3-bromobenzene (0.78 g), palladium acetate (6 mg), and PPh3 (13 mg). The mixture was heated at 600 with vigorous stirring for 22 h. The mixture was allowed to return to room temperature then partitioned between water and EtOAc. The organic phase was washed with brine, dried (MgSO4), and evaporated to dryness. The residual oil was purified on silica SPE bond elut cartridge (50 g) using a gradient of 30%-50% EtOAc in cyclohexane (Gradmaster™). The appropriate fractions were evaporated to give the title compound (1.20 g) LCMS RT=3.91 min.

Workup

  1. temperatureThe mixture was heated at 600
  2. stirringwith vigorous stirring for 22 h
  3. customto return to room temperature
  4. customthen partitioned between water and EtOAc
  5. washThe organic phase was washed with brine
  6. dry with materialdried (MgSO4)
  7. customevaporated to dryness
  8. customThe residual oil was purified on silica SPE bond elut cartridge (50 g)
  9. customThe appropriate fractions were evaporated

Sources & evidence

ORD record
ord-84189d3b72d2410db4dab5ecadca93d9
Source dataset
uspto-grants-2008_10
Patent number
US07442839B2

Reaction notes

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