Water → HCID 59633937, compound

HRID 1615057Notes

Reaction equation

HRID 1615057 reaction equation
[CH:1]1([C:4]2[CH:32]=[CH:31][C:7]([CH2:8][O:9][C:10]3[CH:15]=[CH:14][C:13]([CH:16]4[CH2:19][N:18]([C:20]([C:22]5[CH:27]=[C:26]([OH:28])[CH:25]=[CH:24][N:23]=5)=[O:21])[CH2:17]4)=[CH:12][C:11]=3[O:29][CH3:30])=[CH:6][CH:5]=2)[CH2:3][CH2:2]1.C([O-])([O-])=O.[K+].[K+].C1(C)C=CC(S(O[CH2:49][C@H:50]2[CH2:54][O:53][C:52]([CH3:56])([CH3:55])[O:51]2)(=O)=O)=CC=1.O>CN(C=O)C>[CH:1]1([C:4]2[CH:32]=[CH:31][C:7]([CH2:8][O:9][C:10]3[CH:15]=[CH:14][C:13]([CH:16]4[CH2:19][N:18]([C:20]([C:22]5[CH:27]=[C:26]([O:28][CH2:49][C@H:50]6[CH2:54][O:53][C:52]([CH3:56])([CH3:55])[O:51]6)[CH:25]=[CH:24][N:23]=5)=[O:21])[CH2:17]4)=[CH:12][C:11]=3[O:29][CH3:30])=[CH:6][CH:5]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 6993835(R)-(-)-2,2-Dimethyl-1,3-dioxolan-4-ylmethyl p-ToluenesulfonateHCID 178487635HCID 178487635, compound

Product 1

HCID 59633937HCID 59633937, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a suspension of {3-[4-(4-cyclopropylbenzyloxy)-3-methoxyphenyl]-azetidin-1-yl}-(4-hydroxypyridin-2-yl)-methanone (0.45 g) prepared in a manner similar to Example (6) using 4-hydroxypyridine-2-calboxylic acid and K2CO3 (0.21 g) in DMF (8.0 mL) was added (R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl toluene-4-sulfonate (0.33 g). The reaction mixture was stirred at 100° C. for 13 hr. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, and then dried over MgSO4. The solvent was removed under reduced pressure. The residue was purified by silica gel chromatography (Developing solvent: hexane/ethyl acetate=1/2) to give the title compound (0.27 g, 49%).

Workup

  1. customprepared in a manner similar to Example (6)
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over MgSO4
  5. customThe solvent was removed under reduced pressure
  6. customThe residue was purified by silica gel chromatography (Developing solvent: hexane/ethyl acetate=1/2)

Sources & evidence

ORD record
ord-fbbf6b8cc6b14d5cb79d87729a21e26c
Source dataset
uspto-grants-2014_07
Patent number
US08765739B2

Reaction notes

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