Methanol → HCID 76283582, compound

HRID 624877Notes

Reaction equation

HRID 624877 reaction equation
[C:1]([N:5]([CH2:25][C:26]([O-:28])=[O:27])[C:6](=[O:24])[C:7]1[CH:12]=[CH:11][C:10]([N:13]2[CH2:16][C:15]([F:18])([F:17])[CH2:14]2)=[C:9]([O:19][CH2:20][CH:21]2[CH2:23][CH2:22]2)[N:8]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].C1COCC1.CO>O>[C:1]([N:5]([CH2:25][C:26]([OH:28])=[O:27])[C:6]([C:7]1[CH:12]=[CH:11][C:10]([N:13]2[CH2:14][C:15]([F:17])([F:18])[CH2:16]2)=[C:9]([O:19][CH2:20][CH:21]2[CH2:23][CH2:22]2)[N:8]=1)=[O:24])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 131735192HCID 131735192, compound

Product 1

HCID 76283582HCID 76283582, compoundYield 94.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 2-(N-tert-butyl-6-(cyclopropylmethoxy)-5-(3,3-difluoroazetidin-1-yl)picolinamido)acetate (Example 23, 58 mg, 136 μmol) in a mixture of 1N aqueous NaOH solution (164 μL, 164 μmol), THF (0.5 mL), MeOH (0.2 mL) and water (0.05 mL) was stirred at ambient temperature for 24 h and evaporated to dryness. The residue was partitioned between ice water/0.1N aqueous HCl solution (25 mL) and EtOAc (25 mL). The aqueous layer was extracted one more time with EtOAc (25 mL). The combined extracts were washed with ice/brine (25 mL), dried over Na2SO4 and brought to dryness to give the title compound (51 mg, 128 μmol, 94%) as light yellow solid; MS (EI): m/e=398.4 [MH+].

Workup

  1. customevaporated to dryness
  2. customThe residue was partitioned between ice water/0.1N aqueous HCl solution (25 mL) and EtOAc (25 mL)
  3. extractionThe aqueous layer was extracted one more time with EtOAc (25 mL)
  4. washThe combined extracts were washed with ice/brine (25 mL)
  5. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-4fab913dc8534f94b37cb8dd6a01e4e0
Source dataset
uspto-grants-2016_04
Patent number
US09303012B2

Reaction notes

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