Lithium Hydroxide → 3-[4-(azetidin-1-ylcarbonyl)-2-fluorophenoxy]-5-[(1S)-2-hydroxy-1-methylethoxy]benzoic acid

HRID 20504Notes

Reaction equation

HRID 20504 reaction equation
[N:1]1([C:5]([C:7]2[CH:28]=[CH:27][C:10]([O:11][C:12]3[CH:13]=[C:14]([CH:19]=[C:20]([O:22][C@@H:23]([CH3:26])[CH2:24][OH:25])[CH:21]=3)[C:15]([O:17]C)=[O:16])=[C:9]([F:29])[CH:8]=2)=[O:6])[CH2:4][CH2:3][CH2:2]1.[OH-].[Li+]>C1COCC1.O>[N:1]1([C:5]([C:7]2[CH:28]=[CH:27][C:10]([O:11][C:12]3[CH:13]=[C:14]([CH:19]=[C:20]([O:22][C@@H:23]([CH3:26])[CH2:24][OH:25])[CH:21]=3)[C:15]([OH:17])=[O:16])=[C:9]([F:29])[CH:8]=2)=[O:6])[CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 59346922Methyl 3-[4-(azetidin-1-ylcarbonyl)-2-fluorophenoxy]-5-[(1S)-2-hydroxy-1-methylethoxy]benzoate

Product 1

HCID 593468833-[4-(azetidin-1-ylcarbonyl)-2-fluorophenoxy]-5-[(1S)-2-hydroxy-1-methylethoxy]benzoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 3-[4-(azetidin-1-ylcarbonyl)-2-fluorophenoxy]-5-[(1S)-2-hydroxy-1-methylethoxy]benzoate (100 mg, 0.25 mmol) was dissolved in THF (2.0 mL and water (0.2 mL) and solid lithium hydroxide (21 mg, 0.5 mmol) added. The resultant mixture was stirred at ambient temperature for 16 hours. Water (10 mL) was added and the mixture partially reduced in vacuo and then extracted with ethyl acetate. The aqueous liquors were acidified with 1M hydrochloric acid and re-extracted with ethyl acetate (2×10 mL). The extracts were combined, washed with brine, dried (MgSO4), filtered, and evaporated in vacuo to give the crude product which was used without further purification (70 mg).

Workup

  1. additionadded
  2. extractionextracted with ethyl acetate
  3. extractionre-extracted with ethyl acetate (2×10 mL)
  4. washwashed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-1ecbd50443124bb3bd783689e52ee0b1
Source dataset
uspto-grants-2010_06
Patent number
US07745475B2

Reaction notes

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