Lithium Hydroxide → HCID 18444556, compound

HRID 490355Notes

Reaction equation

HRID 490355 reaction equation
C[O:2][C:3]([C:5]1[O:6][C:7]([CH3:26])=[C:8]([CH2:10][O:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][N:19]=3)=[CH:14][CH:13]=2)[CH:9]=1)=[O:4].[OH-].[Li+]>O1CCCC1.CO>[CH3:25][O:24][C:21]1[CH:22]=[CH:23][C:18]([C:15]2[CH:16]=[CH:17][C:12]([O:11][CH2:10][C:8]3[CH:9]=[C:5]([C:3]([OH:4])=[O:2])[O:6][C:7]=3[CH3:26])=[CH:13][CH:14]=2)=[N:19][CH:20]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 58824205HCID 58824205, compound

Product 1

HCID 18444556HCID 18444556, compound

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A mixture of 4-[4-(5-methoxy-pyridin-2-yl)-phenoxymethyl]-5-methyl-furan-2-carboxylic acid methyl ester (52) (70 mg) and 1M aqueous lithium hydroxide (1 mL) in tetrahydrofuran/methanol (2:1 by volume) (12 mL) was stirred at room temperature for 16 hours. The reaction mixture was acidified to between pH6 and pH7, and partitioned between ethyl acetate and water. The organic phase was separated, washed with brine and dried (MgSO4). After removal of the solvent, the residue was purified by HPLC. Compound 53 was obtained as a solid (2.5 mg). LC/MS System A: Rt=2.90 mins, m/z (ES+)=340 ((M+H) for C19H17NO5).

Workup

  1. custompartitioned between ethyl acetate and water
  2. customThe organic phase was separated
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. customAfter removal of the solvent
  6. customthe residue was purified by HPLC

Sources & evidence

ORD record
ord-7e3a186f795949ee8aec318b27085a87
Source dataset
uspto-grants-2009_05
Patent number
US07528157B2

Reaction notes

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