Lithium Hydroxide → HCID 59496708, compound

HRID 449499Notes

Reaction equation

HRID 449499 reaction equation
[OH-].[Li+].[C:3]([O:7][C:8]([NH:10][CH:11]([CH2:16][C:17]1[CH:18]=[N:19][C:20]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[C:24]=2[F:30])=[CH:21][CH:22]=1)[C:12]([O:14]C)=[O:13])=[O:9])([CH3:6])([CH3:5])[CH3:4]>O.CO>[C:3]([O:7][C:8]([NH:10][CH:11]([CH2:16][C:17]1[CH:18]=[N:19][C:20]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[C:24]=2[F:30])=[CH:21][CH:22]=1)[C:12]([OH:14])=[O:13])=[O:9])([CH3:6])([CH3:4])[CH3:5]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 59496653HCID 59496653, compound

Product 1

HCID 59496708HCID 59496708, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Lithium hydroxide (10 mg, 0.5 mmol) in water (1 mL) was added to a solution of methyl 2-[(tert-butoxycarbonyl)amino]-3-[6-(2,3-difluorophenyl)pyridin-3-yl]propanoate (70 mg, 0.2 mmol) in methanol (3 mL). The reaction was stirred at rt for 3 h. The reaction was concentrated under reduced pressure to remove methanol and was partitioned between EtOAc and ammonium chloride water. The organic was washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure to give crude 2-[(tert-butoxycarbonyl)amino]-3-[6-(2,3-difluorophenyl)pyridin-3-yl]propanoic acid (0.07 g, 100%) as a semisolid residue. Analytical LCMS (M+H)+: m/z=378.9.

Workup

  1. concentrationThe reaction was concentrated under reduced pressure
  2. customto remove methanol
  3. customwas partitioned between EtOAc and ammonium chloride water
  4. washThe organic was washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8245b6958aec4a128c31e0826c13a33f
Source dataset
uspto-grants-2013_07
Patent number
US08481732B2

Reaction notes

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