Hydrochloric Acid → HCID 49806002, compound

HRID 1615060Notes

Reaction equation

HRID 1615060 reaction equation
[CH:1]1([C:4]2[CH:48]=[CH:47][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][O:29][CH2:30][C:31]6([CH2:43][OH:44])[CH2:36][O:35]C(C7C=CC=CC=7)[O:33][CH2:32]6)[CH:25]=[CH:24][N:23]=5)=[O:21])[CH2:17]4)=[CH:12][C:11]=3[O:45][CH3:46])=[CH:6][CH:5]=2)[CH2:3][CH2:2]1.Cl.[OH-].[Na+].C([O-])(O)=O.[Na+]>O1CCCC1>[CH:1]1([C:4]2[CH:48]=[CH:47][C:7]([CH2:8][O:9][C:10]3[CH:15]=[CH:14][C:13]([CH:16]4[CH2:17][N:18]([C:20]([C:22]5[CH:27]=[C:26]([CH2:28][O:29][CH2:30][C:31]([CH2:32][OH:33])([CH2:36][OH:35])[CH2:43][OH:44])[CH:25]=[CH:24][N:23]=5)=[O:21])[CH2:19]4)=[CH:12][C:11]=3[O:45][CH3:46])=[CH:6][CH:5]=2)[CH2:2][CH2:3]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 59634057HCID 59634057, compound2×

Product 1

HCID 49806002HCID 49806002, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the crude {3-[4-(4-cyclopropylbenzyloxy)-3-methoxyphenyl]azetidin-1-yl}-[4-(5-hydroxymethyl-2-phenyl-[1,3]dioxan-5-ylmethoxymethyl)-pyridin-2-yl]-methanone prepared in (1) in THF (10 mL) was added 1 N hydrochloric acid (5.0 mL). The reaction mixture was stirred at RT for 24 hr. To the reaction mixture were added aqueous 1 N NaOH and saturated aqueous NaHCO3 and then the mixture was extracted with ethyl acetate. The organic layer was dried over MgSO4. The solvent was removed under reduced pressure. The residue was purified by silica gel chromatography (Developing solvent: chloroform/methanol=5/1) to give the title compound (0.33 g, 44%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe organic layer was dried over MgSO4
  3. customThe solvent was removed under reduced pressure
  4. customThe residue was purified by silica gel chromatography (Developing solvent: chloroform/methanol=5/1)

Sources & evidence

ORD record
ord-c5d4214a80404bf897b515c0be28a41c
Source dataset
uspto-grants-2014_07
Patent number
US08765739B2

Reaction notes

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