Hydrochloric Acid → HCID 59570937, compound

HRID 2192948Notes

Reaction equation

HRID 2192948 reaction equation
C([O:4][CH2:5][C:6]1[CH:11]=[N:10][C:9]([NH:12][C:13](=[O:37])[C@@H:14]([C:22]2[CH:27]=[CH:26][C:25]([S:28]([CH:31]3[CH2:33][CH2:32]3)(=[O:30])=[O:29])=[C:24]([CH:34]3[CH2:36][CH2:35]3)[CH:23]=2)[CH2:15][CH:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)=[CH:8][N:7]=1)(=O)C.[OH-].[Na+].Cl>CO>[CH:34]1([C:24]2[CH:23]=[C:22]([C@@H:14]([CH2:15][CH:16]3[CH2:17][CH2:18][O:19][CH2:20][CH2:21]3)[C:13]([NH:12][C:9]3[CH:8]=[N:7][C:6]([CH2:5][OH:4])=[CH:11][N:10]=3)=[O:37])[CH:27]=[CH:26][C:25]=2[S:28]([CH:31]2[CH2:32][CH2:33]2)(=[O:29])=[O:30])[CH2:36][CH2:35]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59570911HCID 59570911, compound

Product 1

HCID 59570937HCID 59570937, compoundYield 84.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (5-{[(2R)-2-[3-cyclopropyl-4-(cyclopropylsulfonyl)phenyl]-3-(tetrahydro-2H-pyran-4-yl)propanoyl]amino}pyrazin-2-yl)methyl acetate (120 mg) in methanol (4 mL) was added 1 M aqueous sodium hydroxide solution (1 mL) at room temperature, followed by stirring at room temperature for 2 hours. 1 M Hydrochloric acid was added to adjust the pH to 3, followed by extraction with ethyl acetate. The organic layer was washed with saturated aqueous sodium bicarbonate and saturated brine, and dried over anhydrous magnesium sulfate. The crude product obtained by concentration was purified by silica gel column chromatography (wetting with hexane:ethyl acetate=1:1, chloroform:methanol=1:0-10:1) to obtain (2R)-2-[3-cyclopropyl-4-(cyclopropylsulfonyl)phenyl]-N-[5-(hydroxymethyl)pyrazin-2-yl]-3-(tetrahydro-2H-pyran-4-yl)propanamide (93 mg) as a white amorphous substance.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with saturated aqueous sodium bicarbonate and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe crude product obtained by concentration
  5. customwas purified by silica gel column chromatography (wetting with hexane:ethyl acetate=1:1, chloroform:methanol=1:0-10:1)

Sources & evidence

ORD record
ord-1c73c3d3caa44eeb84e274bb5e9a8057
Source dataset
uspto-grants-2012_12
Patent number
US08329707B2

Reaction notes

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