Sodium Hydroxide → HCID 59331458, compound

HRID 1882070Notes

Reaction equation

HRID 1882070 reaction equation
[CH:1]1([S:4]([C:7]2[CH:12]=[CH:11][C:10]([CH:13]([CH2:31][CH:32]3[CH2:37][CH2:36][O:35][CH2:34][CH2:33]3)[C:14](=O)[CH2:15][CH2:16][C:17]([C:19]3[N:20]=[CH:21][N:22]([CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH:23]=3)=O)=[CH:9][CH:8]=2)(=[O:6])=[O:5])[CH2:3][CH2:2]1.C([O-])(=O)C.[NH4+:42].[OH-].[Na+]>C(O)(=O)C>[CH:1]1([S:4]([C:7]2[CH:8]=[CH:9][C:10]([CH:13]([C:14]3[NH:42][C:17]([C:19]4[N:20]=[CH:21][N:22]([CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH:23]=4)=[CH:16][CH:15]=3)[CH2:31][CH:32]3[CH2:33][CH2:34][O:35][CH2:36][CH2:37]3)=[CH:11][CH:12]=2)(=[O:6])=[O:5])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 517165Ammonium AcetateHCID 59331394HCID 59331394, compound

Product 1

HCID 59331458HCID 59331458, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of ethyl (4-{5-[4-(cyclopropylsulfonyl)phenyl]-4-oxo-6-(tetrahydro-2H-pyran-4-yl)hexanoyl}-1H-imidazol-1-yl)acetate (1.05 g), ammonium acetate (0.70 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 fraction eluted with ethyl acetate was concentrated. The obtained residue was subjected to silica gel column chromatography, and the title compound (0.44 g, yield 51%) was obtained as a pale-yellow amorphous solid from a fraction eluted with tetrahydrofuran-hexane (5:1, volume ratio). MS: 512 (MH+).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. washthe fraction eluted with ethyl acetate
  6. concentrationwas concentrated

Sources & evidence

ORD record
ord-d4c974c7af604fe29ffa035605cef20f
Source dataset
uspto-grants-2012_11
Patent number
US08318746B2

Reaction notes

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