Water → HCID 89497975, compound

HRID 1778922Notes

Reaction equation

HRID 1778922 reaction equation
[CH2:1]([O:4][C:5]1([CH2:11][N:12]2[C:16]([CH3:17])=[C:15]([Br:18])[CH:14]=[N:13]2)[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1)[CH:2]=C.N1C(C)=CC=CC=1C.[OH2:27].ClCCl>O1CCOCC1.O.O=[Os](=O)(=O)=O>[Br:18][C:15]1[CH:14]=[N:13][N:12]([CH2:11][C:5]2([O:4][CH2:1][CH:2]=[O:27])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]2)[C:16]=1[CH3:17]

Participants

7

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 79372,6-LutidineHCID 89498099HCID 89498099, compound

Product 1

HCID 89497975HCID 89497975, compound

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

To a solution of EXAMPLE 167B (3.13 g) in dioxane/water (3:1, 40 mL) was added 2,6-lutidine (2.5 mL), OsO4 (2.5% in tert-butanol, 2.75 mL), and NaIO4 (8.55 g) under argon. The reaction mixture was stirred at room temperature for 4 hours, then water (50 mL) and dichloromethane (200 mL) were added. The organic layer was separated, and the water phase was extracted by dichloromethane (3×200 mL). The combined organic layers were washed with brine (200 mL) and dried over Na2SO4. After filtration, the solvent was removed to give the crude product which was used in the next step without further purification.

Workup

  1. customThe organic layer was separated
  2. extractionthe water phase was extracted by dichloromethane (3×200 mL)
  3. washThe combined organic layers were washed with brine (200 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationAfter filtration
  6. customthe solvent was removed

Sources & evidence

ORD record
ord-cc55ac212d554df3a3908362348b7e43
Source dataset
uspto-grants-2016_02
Patent number
US09266877B2

Reaction notes

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