Sodium Hydroxide → HCID 71087631, compound

HRID 632306Notes

Reaction equation

HRID 632306 reaction equation
C[O:2][C:3](=[O:28])[C:4]([NH:9][C:10]([C:12]1[CH:17]=[CH:16][C:15]([CH:18]2[CH2:20][CH2:19]2)=[C:14]([O:21][CH2:22][CH:23]2[CH2:27][CH2:26][CH2:25][O:24]2)[N:13]=1)=[O:11])([CH2:7][CH3:8])[CH2:5][CH3:6].O.[OH-].[Li+].[OH-].[Na+]>C1COCC1.O>[CH:18]1([C:15]2[CH:16]=[CH:17][C:12]([C:10]([NH:9][C:4]([CH2:7][CH3:8])([CH2:5][CH3:6])[C:3]([OH:28])=[O:2])=[O:11])=[N:13][C:14]=2[O:21][CH2:22][CH:23]2[CH2:27][CH2:26][CH2:25][O:24]2)[CH2:20][CH2:19]1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 168937Lithium hydroxide, monohydrateHCID 710876662-{[5-Cyclopropyl-6-(tetrahydro-furan-2-ylmethoxy)-pyridine-2-carbonyl]-amino}-2-ethyl-butyric acid methyl ester

Product 1

HCID 71087631HCID 71087631, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl 2-(5-cyclopropyl-6-((tetrahydrofuran-2-yl)methoxy)picolinamido)-2-ethylbutanoate (60 mg, 154 μmol, Example 233) and lithium hydroxide hydrate (7.74 mg, 184 μmol) were dissolved in a mixture of THF (600 μL) and water (150 μL). The reaction mixture was stirred for 48 h at ambient temp. Additional sodium hydroxide (24.6 mg, 614 μmol) was added and stirring was continued at 70° C. for additional 3 d. The mixture was poured onto ice water/brine/1N HCl (25 mL) and extracted with EtOAc (2×30 mL). The combined extracts were washed with ice water/brine (25 mL) and dried over Na2SO4. Concentration in vacuo afforded the title compound (49 mg, 85%) as a light yellow waxy solid. MS: 375.3 [M−H]−.

Workup

  1. stirringstirring
  2. waitwas continued at 70° C. for additional 3 d
  3. additionThe mixture was poured onto ice water/brine/1N HCl (25 mL)
  4. extractionextracted with EtOAc (2×30 mL)
  5. washThe combined extracts were washed with ice water/brine (25 mL)
  6. dry with materialdried over Na2SO4
  7. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-1bb7a86405eb46b7a12cf0d1f34af0f6
Source dataset
uspto-grants-2016_04
Patent number
US09321727B2

Reaction notes

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