Ethanol → HCID 59331324, compound

HRID 1882042Notes

Reaction equation

HRID 1882042 reaction equation
[CH:1]1([S:4]([C:7]2[CH:12]=[CH:11][C:10]([CH:13]([C:21]3[NH:25][C:24]([C:26]4[N:31]=[CH:30]C(CC#N)=C[CH:27]=4)=[CH:23][CH:22]=3)[CH2:14][CH:15]3CCO[CH2:17][CH2:16]3)=[CH:9][CH:8]=2)(=[O:6])=[O:5])[CH2:3][CH2:2]1.[O:35]1[CH2:39][CH2:38][CH2:37][CH2:36]1.[CH2:40]([OH:42])[CH3:41].[OH-:43].[Na+]>C(O)(=O)C>[CH:1]1([S:4]([C:7]2[CH:8]=[CH:9][C:10]([CH:13]([C:21]3[NH:25][C:24]([C:26]4[N:31]=[CH:30][C:37]([CH2:38][C:39]([OH:35])=[O:43])=[CH:36][CH:27]=4)=[CH:23][CH:22]=3)[CH2:14][CH:15]3[CH2:16][CH2:17][O:42][CH2:40][CH2:41]3)=[CH:11][CH:12]=2)(=[O:6])=[O:5])[CH2:2][CH2:3]1

Participants

6

Reactant 4

HCID 702EthanolHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 59331350HCID 59331350, compound

Product 1

HCID 59331324HCID 59331324, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of [6-(5-{1-[4-(cyclopropylsulfonyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl}-1H-pyrrol-2-yl)pyridin-3-yl]acetonitrile (0.200 g) in a mixed solvent of tetrahydrofuran (3 mL) and ethanol (3 mL) was added 4M aqueous sodium hydroxide solution (3 mL), and the mixture was stirred at 90° C. for 16 hr. The reaction mixture was acidified with acetic acid, and extracted with ethyl acetate. The extract was washed successively with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:methanol=100:0-80:20, volume ratio) to give the title compound (0.131 g, yield 63%) as a yellow amorphous solid. MS: 495 (MH+). melting point 124-127° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed successively with water and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate:methanol=100:0-80:20, volume ratio)

Sources & evidence

ORD record
ord-538b069b7df641b68da7c2f7270fb43e
Source dataset
uspto-grants-2012_11
Patent number
US08318746B2

Reaction notes

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