Water → HCID 22881398, compound

HRID 726673Notes

Reaction equation

HRID 726673 reaction equation
ClC(OC(Cl)(Cl)Cl)=O.[CH:9]1([O:14][C:15]2[CH:16]=[C:17]([C@@H:23]([C:31]3[CH:39]=[CH:38][C:34]([CH:35]=[N:36]O)=[CH:33][CH:32]=3)[CH2:24][C:25]3[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=3)[CH:18]=[CH:19][C:20]=2[O:21][CH3:22])[CH2:13][CH2:12][CH2:11][CH2:10]1.O>C(#N)C>[CH:9]1([O:14][C:15]2[CH:16]=[C:17]([C@@H:23]([C:31]3[CH:32]=[CH:33][C:34]([C:35]#[N:36])=[CH:38][CH:39]=3)[CH2:24][C:25]3[CH:26]=[CH:27][N:28]=[CH:29][CH:30]=3)[CH:18]=[CH:19][C:20]=2[O:21][CH3:22])[CH2:10][CH2:11][CH2:12][CH2:13]1

Participants

5

Reactant 3

HCID 962WaterHCID 10426DiphosgeneHCID 88131815HCID 88131815, compound

Product 1

HCID 22881398HCID 22881398, compoundYield 87.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Trichloromethyl chloroformate (0.18 mL, 1.5 mmol) was added to a 0° C. solution of (R)-4-[1-(3-cyclopentyloxy-4-methoxyphenyl)-2-(4-pyridyl)ethyl]benzaldehyde oxime from Example 3 (425 mg, 1.0 mmol) in acetonitrile (4 mL). The reaction mixture was stirred at room temperature for 1 hour before water was added. The mixture was then extracted with EtOAc. The organic phase was washed with 5% aqueous NaHCO3, water and brine, dried (MgSO4) and evaporated to afford the title compound as an off-white solid (350 mg, 86%).

Workup

  1. additionwas added
  2. extractionThe mixture was then extracted with EtOAc
  3. washThe organic phase was washed with 5% aqueous NaHCO3, water and brine
  4. dry with materialdried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-cd1a1c0e9f6e4590b3f80f37ec925214
Source dataset
uspto-grants-1998_01
Patent number
US05710160

Reaction notes

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