Acetonitrile → HCID 45110900, compound

HRID 386914Notes

Reaction equation

HRID 386914 reaction equation
[C:1]([N:4](CC1C=CC(OC)=CC=1)[CH2:5][C:6]([C:9]1[CH:13]=[C:12]([NH:14][C:15](=[O:28])[C:16]([CH3:27])([S:18]([CH:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)(=[O:20])=[O:19])[CH3:17])[O:11][N:10]=1)([CH3:8])[CH3:7])(=[O:3])[CH3:2].C(#N)C>O>[C:1]([NH:4][CH2:5][C:6]([C:9]1[CH:13]=[C:12]([NH:14][C:15](=[O:28])[C:16]([CH3:17])([S:18]([CH:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)(=[O:20])=[O:19])[CH3:27])[O:11][N:10]=1)([CH3:8])[CH3:7])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 6342AcetonitrileHCID 59253295HCID 59253295, compound

Product 1

HCID 45110900HCID 45110900, compoundYield 4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of N-(3-{2-[acetyl-(4-methoxy-benzyl)-amino]-1,1-dimethyl-ethyl}-isoxazol-5-yl)-2-methyl-2-(tetrahydro-pyran-4-sulfonyl)-propionamide (116 mg, 0.22 mmol) in the mixture of acetonitrile (2 mL) and water (0.7 mL) is added ceric ammonium nitrate (476 mg, 0.87 mmol). The reaction mixture is stirred at room temperature for 40 minutes. After this time, the reaction mixture is quenched with saturated aqueous NaHCO3 solution and extracted with ethyl acetate 3 times. The organics are combined and washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. Purification by preparative HPLC provides the title compound. Yield: 4%; m/z 416 [M+H].

Workup

  1. customAfter this time, the reaction mixture is quenched with saturated aqueous NaHCO3 solution
  2. extractionextracted with ethyl acetate 3 times
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customPurification by preparative HPLC

Sources & evidence

ORD record
ord-2180c80cc2f942719f699ab27b5b232f
Source dataset
uspto-grants-2013_02
Patent number
US08372874B2

Reaction notes

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