Water → HCID 66786530, compound

HRID 1615055Notes

Reaction equation

HRID 1615055 reaction equation
[CH3:1][C:2]1([CH3:9])[O:6][C@H:5]([CH2:7][OH:8])[CH2:4][O:3]1.[H-].[Na+].CS(OC[C:18]1[CH:23]=[CH:22][N:21]=[C:20]([C:24]([N:26]2[CH2:29][CH:28]([C:30]3[CH:35]=[CH:34][C:33]([O:36][CH2:37][C:38]4[CH:43]=[CH:42][C:41]([CH:44]5[CH2:46][CH2:45]5)=[CH:40][CH:39]=4)=[C:32]([O:47][CH3:48])[CH:31]=3)[CH2:27]2)=[O:25])[CH:19]=1)(=O)=O.O.[CH3:50]N(C=O)C>>[CH:44]1([C:41]2[CH:40]=[CH:39][C:38]([CH2:37][O:36][C:33]3[CH:34]=[CH:35][C:30]([CH:28]4[CH2:29][N:26]([C:24]([C:20]5[CH:19]=[C:18]([C@H:7]([CH:5]6[CH2:4][O:3][C:2]([CH3:9])([CH3:1])[O:6]6)[O:8][CH3:50])[CH:23]=[CH:22][N:21]=5)=[O:25])[CH2:27]4)=[CH:31][C:32]=3[O:47][CH3:48])=[CH:43][CH:42]=2)[CH2:46][CH2:45]1

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 736056(R)-SolketalHCID 59634043HCID 59634043, compound2×

Product 1

HCID 66786530HCID 66786530, compound

Procedure

To a solution of (R)-(−)-2,2-dimethyl-1,3-dioxolan-4-methanol (0.42 mL) in DMF (10 mL) was added NaH (0.14 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 (0.80 g) prepared in (7). The reaction mixture was stirred for 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, reduced pressure to give the crude title compound.

Workup

  1. stirringThe reaction mixture was stirred for at RT for 1 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water, reduced pressure

Sources & evidence

ORD record
ord-2aee4bf1dc3e43af89e60c2291d7ff11
Source dataset
uspto-grants-2014_07
Patent number
US08765739B2

Reaction notes

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