Water → HCID 59633892, compound

HRID 1615066Notes

Reaction equation

HRID 1615066 reaction equation
[CH2:1]([C:3]1[CH:34]=[CH:33][C:6]([CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([CH:15]3[CH2:18][N:17]([C:19]([C:21]4[CH:26]=[C:25]([O:27][CH2:28][CH2:29][OH:30])[CH:24]=[CH:23][N:22]=4)=[O:20])[CH2:16]3)=[CH:11][C:10]=2[O:31][CH3:32])=[CH:5][CH:4]=1)[CH3:2].C(N(CC)CC)C.[CH3:42][S:43](Cl)(=[O:45])=[O:44].O>O1CCCC1>[CH3:42][S:43]([O:30][CH2:29][CH2:28][O:27][C:25]1[CH:24]=[CH:23][N:22]=[C:21]([C:19]([N:17]2[CH2:16][CH:15]([C:12]3[CH:13]=[CH:14][C:9]([O:8][CH2:7][C:6]4[CH:5]=[CH:4][C:3]([CH2:1][CH3:2])=[CH:34][CH:33]=4)=[C:10]([O:31][CH3:32])[CH:11]=3)[CH2:18]2)=[O:20])[CH:26]=1)(=[O:45])=[O:44]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 59634061HCID 59634061, compound

Product 1

HCID 59633892HCID 59633892, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of {3-[4-(4-ethylbenzyloxy)-3-methoxyphenyl]azetidin-1-yl}-[4-(2-hydroxyethoxy)pyridin-2-yl]-methanone (8.49 g) prepared in Example 5 in THF (45 mL) were added triethylamine (2.8 mL) and methanesulfonyl chloride (1.5 mL) at 0° C. The reaction mixture was stirred at RT for 30 min. 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 Na2SO4. The solvent was removed under reduced pressure. Diisopropyl ether was added to the residue. The precipitated solid was collected on a filter and dried to give the title compound (9.5 g, 97%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over Na2SO4
  4. customThe solvent was removed under reduced pressure
  5. additionDiisopropyl ether was added to the residue
  6. customThe precipitated solid was collected on
  7. filtrationa filter
  8. customdried

Sources & evidence

ORD record
ord-1384a3144b4c4ae28dd069a55abc4e1b
Source dataset
uspto-grants-2014_07
Patent number
US08765739B2

Reaction notes

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