Sodium Hydroxide → HCID 59331498, compound

HRID 1882067Notes

Reaction equation

HRID 1882067 reaction equation
[OH:1][CH:2]([C:7]1[CH:8]=[CH:9][C:10]([C:13](=O)[CH2:14][CH2:15][C:16](=O)[CH:17]([C:25]2[CH:30]=[CH:29][C:28]([S:31][CH3:32])=[CH:27][N:26]=2)[CH2:18][CH:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)=[N:11][CH:12]=1)[C:3]([OH:6])([CH3:5])[CH3:4].C([O-])(=O)C.[NH4+:39].[OH-].[Na+]>C(O)(=O)C>[CH3:4][C:3]([OH:6])([CH3:5])[CH:2]([C:7]1[CH:12]=[N:11][C:10]([C:13]2[NH:39][C:16]([CH:17]([C:25]3[CH:30]=[CH:29][C:28]([S:31][CH3:32])=[CH:27][N:26]=3)[CH2:18][CH:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)=[CH:15][CH:14]=2)=[CH:9][CH:8]=1)[OH:1]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 517165Ammonium AcetateHCID 593312671-[5-(1,2-dihydroxy-2-methylpropyl)pyridin-2-yl]-5-[5-(methylsulfanyl)pyridin-2-yl]-6-(tetrahydro-2H-pyran-4-yl)hexane-1,4-dione

Product 1

HCID 59331498HCID 59331498, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 1-[5-(1,2-dihydroxy-2-methylpropyl)pyridin-2-yl]-5-[5-(methylsulfanyl)pyridin-2-yl]-6-(tetrahydro-2H-pyran-4-yl)hexane-1,4-dione (0.49 g), ammonium acetate (0.39 g) and acetic acid (5 mL) was stirred at 80° C. for 3 hr. The reaction mixture was neutralized with 8M aqueous sodium hydroxide solution, and extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The residue was subjected to basic silica gel column chromatography, and the title compound (0.37 g, yield 79%) was obtained as a colorless amorphous form from a fraction eluted with ethyl acetate. MS: 468 (MH+).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-a01a89e8f66d48ddb4e67b873485a485
Source dataset
uspto-grants-2012_11
Patent number
US08318746B2

Reaction notes

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