Sodium Phosphate, Dibasic → HCID 58574019, compound

HRID 932286Notes

Reaction equation

HRID 932286 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@H:8]([C@@:13]([C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=2)([NH:15][CH:16]([CH3:18])[CH3:17])[CH3:14])[CH2:9][CH2:10][CH2:11][OH:12])[CH:5]=[CH:6][CH:7]=1.I(O)(=O)(=O)=[O:27].P([O-])([O-])(O)=O.[Na+].[Na+]>C(#N)C.O.[O-2].[O-2].[O-2].[Cr+6]>[Cl:1][C:2]1[CH:3]=[C:4]([C@H:8]([C@@:13]([C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=2)([NH:15][CH:16]([CH3:18])[CH3:17])[CH3:14])[CH2:9][CH2:10][C:11]([OH:27])=[O:12])[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 3

HCID 24203Sodium Phosphate, DibasicHCID 65185Metaperiodic acidHCID 58573203HCID 58573203, compound

Product 1

HCID 58574019HCID 58574019, compound

Reagents, catalysts & solvents 3

HCID 10219390chromium (VI) trioxideCatalystHCID 962WaterSolvent3×HCID 6342AcetonitrileSolvent2×

Procedure

To a solution of (4R,5S)-4-(3-chlorophenyl)-5-(4-chlorophenyl)-5-(isopropylamino)hexan-1-ol (Example 418, Step F, 185 mg, 0.486 mmol) in wet acetonitrile (0.75% water v/v) (3 mL) at ambient temperature was added over three minutes a solution of periodic acid (0.44M in acetonitrile(0.75% water v/v), 2.76 mL, 1.216 mmol) with chromium trioxide (2.43 mg, 0.024 mmol). The reaction was stirred for fifteen minutes. To the reaction was added a solution of 0.6 g disodium hydrogen phosphate in 10 mL water. The aqueous mixture was extracted with toluene. The organic layer was washed with water/brine then with a solution of 0.2 g sodium hydrogen sulfite in 5 mL water. The organic layer was then dried with anhydrous magnesium sulfate and concentrated to afford a peach-colored foamy solid. The product was isolated by chromatography on silica (24 g RediSep® pre-packed silica gel column (Teledyne Isco, Lincoln, Nebr.)) eluting with 50-100% ethyl acetate gradient in hexane to afford the title compound as a colorless foam.

Workup

  1. extractionThe aqueous mixture was extracted with toluene
  2. washThe organic layer was washed with water/brine
  3. dry with materialThe organic layer was then dried with anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customto afford a peach-colored foamy solid
  6. customThe product was isolated by chromatography on silica (24 g RediSep® pre-packed silica gel column (Teledyne Isco, Lincoln, Nebr.))
  7. washeluting with 50-100% ethyl acetate gradient in hexane

Sources & evidence

ORD record
ord-dfbfb5aa354841b29ccc34ea648f5506
Source dataset
uspto-grants-2016_03
Patent number
US09296736B2

Reaction notes

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