Tetrahydrofuran → (S)-4-(1,2-dihydroxyethyl)-6-(4-(4-fluorophenoxy)phenyl)picolinic acid

HRID 2271398Notes

Reaction equation

HRID 2271398 reaction equation
[OH:1][C@@H:2]([C:5]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([O:17][C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)=[CH:13][CH:12]=2)[N:8]=[C:7]([C:25]([O:27]C)=[O:26])[CH:6]=1)[CH2:3][OH:4].C1COCC1.O[Li].O>O>[OH:1][C@@H:2]([C:5]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([O:17][C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)=[CH:13][CH:12]=2)[N:8]=[C:7]([C:25]([OH:27])=[O:26])[CH:6]=1)[CH2:3][OH:4]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 66668464(S)-methyl 4-(1,2-dihydroxyethyl)-6-(4-(4-fluorophenoxy)phenyl)picolinate

Product 1

HCID 66668271(S)-4-(1,2-dihydroxyethyl)-6-(4-(4-fluorophenoxy)phenyl)picolinic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To the crude (S)-methyl 4-(1,2-dihydroxyethyl)-6-(4-(4-fluorophenoxy)phenyl)picolinate (assume 0.884 mmol) in 5 mL of a 5:1 mixture of THF and water was added LiOH.H2O (0.084 g, 2.00 mmol). The reaction was stirred overnight then evaporated in vacuo. The residue was dissolved in 5 mL water, filtered and acidified with 2.00 mL 1N HCl. The mixture was evaporated in vacuo to give the product (S)-4-(1,2-dihydroxyethyl)-6-(4-(4-fluorophenoxy)phenyl)picolinic acid mixed with lithium chloride (LC/MS: m/z=370.2 [M+H]+).

Workup

  1. customthen evaporated in vacuo
  2. dissolutionThe residue was dissolved in 5 mL water
  3. filtrationfiltered
  4. customThe mixture was evaporated in vacuo

Sources & evidence

ORD record
ord-23292a138d554335ad750e47d2e6f613
Source dataset
uspto-grants-2015_09
Patent number
US09120752B2

Reaction notes

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