Water → 1,1-Dimethylethyl methyl[2-({4-[(phenylmethyl)oxy]-3-[(3-pyridinylamino)carbonyl]phenyl}oxy)ethyl]carbamate

HRID 1623697Notes

Reaction equation

HRID 1623697 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[C:6]([CH:16]=1)[C:7]([NH:9][C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1)=[O:8].[H-].[Na+].CC1C=CC(S(O[CH2:38][CH2:39][N:40]([C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])[CH3:41])(=O)=O)=CC=1.O>CS(C)=O>[CH3:41][N:40]([CH2:39][CH2:38][O:1][C:2]1[CH:3]=[CH:4][C:5]([O:17][CH2:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[C:6]([C:7]([NH:9][C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)=[O:8])[CH:16]=1)[C:42](=[O:43])[O:44][C:45]([CH3:46])([CH3:48])[CH3:47]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 215811562-(tert-Butoxycarbonyl(methyl)amino)-ethyl 4-methylbenzenesulfonateHCID 513575145-hydroxy-2-[(phenylmethyl)oxy]-N-3-pyridinylbenzamide

Product 1

HCID 681081751,1-Dimethylethyl methyl[2-({4-[(phenylmethyl)oxy]-3-[(3-pyridinylamino)carbonyl]phenyl}oxy)ethyl]carbamate

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

To a solution of 5-hydroxy-2-[(phenylmethyl)oxy]-N-3-pyridinylbenzamide (may be prepared as described in Example 44; 200 mg, 0.62 mmol) in dimethylsulfoxide (8 ml) was added sodium hydride (17.98 mg, 0.75 mmol) at 0° C., and the mixture was stirred at room temperature for 1 h. 2-[{[(1,1-Dimethylethyl)oxy]carbonyl}(methyl)amino]ethyl 4-methylbenzenesulfonate (247 mg, 0.75 mmol) in dimethylsulfoxide (8 ml) was added to the solution dropwise, and the mixture was stirred at 75° C. for 18 h. The mixture was poured into water (100 ml), extracted thoroughly with ethyl acetate. The organic layer was dried, and concentrated to obtain a crude product. The crude product was purified by chromatography on silica gel (dichloromethane/methanol=15:1) to yield the title compound as a yellow oil. 140 mg.

Workup

  1. stirringthe mixture was stirred at 75° C. for 18 h
  2. extractionextracted thoroughly with ethyl acetate
  3. customThe organic layer was dried
  4. concentrationconcentrated
  5. customto obtain a crude product
  6. customThe crude product was purified by chromatography on silica gel (dichloromethane/methanol=15:1)

Sources & evidence

ORD record
ord-8bf1fb42a5014dc5a973f2fc385e70e6
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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