Sodium Hydroxide → HCID 5273767, compound

HRID 1351730Notes

Reaction equation

HRID 1351730 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][CH2:8][O:7]1)=[C:17]([C:19]#[N:20])[C:16]([F:21])=[CH:15][C:14]=3[CH3:22])C.[OH-].[Na+]>C1COCC1.CO>[C:19]([C:17]1[C:16]([F:21])=[CH:15][C:14]([CH3:22])=[C:13]2[C:18]=1[C:10]1[CH2:9][CH2:8][O:7][C:6]([CH2:23][CH2:24][CH3:25])([CH2:5][C:4]([OH:26])=[O:3])[C:11]=1[NH:12]2)#[N:20]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 23401459HCID 23401459, compound

Product 1

HCID 5273767HCID 5273767, compoundYield 91.3%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of 5-cyano-6-fluoro-8-methyl-1-propyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetic acid ethyl ester (404 mg, 1.13 mmol) in THF/MeOH (2.5 mL/5 mL) was added 1 N NaOH (2.26 mL, 2.26 mmol). The reaction mixture was stirred at ambient temperature overnight. Most of the 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 to provide 341 mg (91%) of title compound as a white solid. 1H NMR (DMSO): 300 MHz δ 12.02 (bs, 1H), 11.33 (bs, 1H), 7.00 (d, J=9.00 Hz, 1H), 3.96 (m, 2H), 2.95 (d, J=10.3 Hz, 1H), 2.83 (t, J=3.9 Hz, 1H), 2.72 (d, J=10.3 Hz, 1H), 2.54 (s, 3H), 1.99 (m, 2H), 1.28 (m, 1H), 0.85 (m, 1H), 0.79 (t, J=5.41 Hz, 3H).

Workup

  1. customMost of the 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

Sources & evidence

ORD record
ord-9ce9604dbd64480ea403867f4da2aeb9
Source dataset
uspto-grants-2007_05
Patent number
US07217730B2

Reaction notes

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