Sodium Hydroxide → HCID 21099081, compound

HRID 1351744Notes

Reaction equation

HRID 1351744 reaction equation
C([O:3][C:4](=[O:26])[CH2:5][C:6]1([CH2:23][CH2:24][CH3:25])[C:11]2[NH:12][C:13]3[C:18]([C:10]=2[CH2:9][CH:8]([CH3:22])[O:7]1)=[C:17]([C:19]#[N:20])[CH:16]=[CH:15][C:14]=3[F:21])C.[OH-].[Na+]>C1COCC1.CO>[C:19]([C:17]1[CH:16]=[CH:15][C:14]([F:21])=[C:13]2[C:18]=1[C:10]1[CH2:9][CH:8]([CH3:22])[O:7][C:6]([CH2:5][C:4]([OH:26])=[O:3])([CH2:23][CH2:24][CH3:25])[C:11]=1[NH:12]2)#[N:20]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69424878HCID 69424878, compound

Product 1

HCID 21099081HCID 21099081, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of (5-cyano-8-fluoro-3-methyl-1-propyl-1,3,4,9-tetrahydro-pyrano[3,4-b]indol-1-yl)-acetic Acid Ethyl Ester (156 mg, 0.435 mmol) in THF/MeOH (1.5 mL/1.5 mL) was added 1 N NaOH (0.871 mL, 0.871 mmol). The reaction mixture was stirred at ambient temperature overnight. The most of THF/MeOH was removed under reduced pressure and the resulting mixture was acidified with 1 N HCl. The mixture was extracted with EtOAc (3×10 mL). The combined organic phase was washed with brine (20 mL), dried over Na2SO4 and concentrated. The residue was purified by preparative HPLC to give 125 mg (87%) of title compound as a white solid. LCMS retention time: 2.775 minutes, [M+H]+ calculated for C18H20FN2O3 331.36, found 331.10, [M−1]+ calculated for C18H18FN2O 329.36, found 329.10.

Workup

  1. customThe most of THF/MeOH was removed under reduced pressure
  2. extractionThe mixture was extracted with EtOAc (3×10 mL)
  3. washThe combined organic phase was washed with brine (20 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-c8ef5e4a562c4a14bd750d833cd662ee
Source dataset
uspto-grants-2007_05
Patent number
US07217730B2

Reaction notes

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