Water → HCID 59634043, compound

HRID 1615054Notes

Reaction equation

HRID 1615054 reaction equation
[CH:1]1([C:4]2[CH:33]=[CH:32][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]([CH2:28][OH:29])[CH:25]=[CH:24][N:23]=5)=[O:21])[CH2:17]4)=[CH:12][C:11]=3[O:30][CH3:31])=[CH:6][CH:5]=2)[CH2:3][CH2:2]1.C(N(CC)CC)C.[CH3:41][S:42](Cl)(=[O:44])=[O:43].O>C(Cl)(Cl)Cl>[CH3:41][S:42]([O:29][CH2:28][C:26]1[CH:25]=[CH:24][N:23]=[C:22]([C:20]([N:18]2[CH2:17][CH:16]([C:13]3[CH:14]=[CH:15][C:10]([O:9][CH2:8][C:7]4[CH:32]=[CH:33][C:4]([CH:1]5[CH2:3][CH2:2]5)=[CH:5][CH:6]=4)=[C:11]([O:30][CH3:31])[CH:12]=3)[CH2:19]2)=[O:21])[CH:27]=1)(=[O:44])=[O:43]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 59633911HCID 59633911, compound2×

Product 1

HCID 59634043HCID 59634043, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of {3-[4-(4-cyclopropylbenzyloxy)-3-methoxyphenyl]azetidin-1-yl}-(4-hydroxymethylpyridin-2-yl)-methanone (4.0 g) prepared in (6) in chloroform (80 mL) were added triethylamine (3.0 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 chloroform. The organic layer was dried over MgSO4. The solvent was removed under reduced pressure. Hexane was added to the residue. The precipitated solid was collected on a filter and dried to give the title compound (4.6 g, 99%).

Workup

  1. extractionthe mixture was extracted with chloroform
  2. dry with materialThe organic layer was dried over MgSO4
  3. customThe solvent was removed under reduced pressure
  4. additionHexane was added to the residue
  5. customThe precipitated solid was collected on
  6. filtrationa filter
  7. customdried

Sources & evidence

ORD record
ord-186027dec39341bea25df95f6a823632
Source dataset
uspto-grants-2014_07
Patent number
US08765739B2

Reaction notes

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