Water → HCID 59634057, compound

HRID 1615059Notes

Reaction equation

HRID 1615059 reaction equation
[OH:1][CH2:2][C:3]1([CH2:15][OH:16])[CH2:8][O:7][CH:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[O:5][CH2:4]1.[H-].[Na+].CS(O[CH2:24][C:25]1[CH:30]=[CH:29][N:28]=[C:27]([C:31]([N:33]2[CH2:36][CH:35]([C:37]3[CH:42]=[CH:41][C:40]([O:43][CH2:44][C:45]4[CH:50]=[CH:49][C:48]([CH:51]5[CH2:53][CH2:52]5)=[CH:47][CH:46]=4)=[C:39]([O:54][CH3:55])[CH:38]=3)[CH2:34]2)=[O:32])[CH:26]=1)(=O)=O.O>CN(C=O)C>[CH:51]1([C:48]2[CH:49]=[CH:50][C:45]([CH2:44][O:43][C:40]3[CH:41]=[CH:42][C:37]([CH:35]4[CH2:34][N:33]([C:31]([C:27]5[CH:26]=[C:25]([CH2:24][O:16][CH2:15][C:3]6([CH2:2][OH:1])[CH2:4][O:5][CH:6]([C:9]7[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=7)[O:7][CH2:8]6)[CH:30]=[CH:29][N:28]=5)=[O:32])[CH2:36]4)=[CH:38][C:39]=3[O:54][CH3:55])=[CH:46][CH:47]=2)[CH2:53][CH2:52]1

Participants

6

Reactant 4

HCID 962WaterHCID 17042Mono-o-benzylidinepentaerythritolHCID 24758Sodium hydrideHCID 59634043HCID 59634043, compound

Product 1

HCID 59634057HCID 59634057, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (5-hydroxymethyl-2-phenyl-[1,3]dioxan-5-yl)methanol (0.66 g) in DMF (10 mL) was added NaH (0.12 g). The mixture was stirred at RT for 1 hr. To the mixture was added 2-{3-[4-(4-cyclopropylbenzyloxy)-3-methoxyphenyl]azetidine-1-carbonyl}pyridin-4-ylmethyl methanesulfonate (0.7 g) prepared in Example 1 (7). The reaction mixture was stirred at RT for 1 hr. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with water, and then dried over MgSO4. The solvent was removed under reduced pressure to give the crude title compound.

Workup

  1. stirringThe reaction mixture was stirred at RT for 1 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialdried over MgSO4
  5. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-105fbc1a745c44b09dee676c9fe90d76
Source dataset
uspto-grants-2014_07
Patent number
US08765739B2

Reaction notes

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