Hydrochloric Acid → HCID 59226525, compound

HRID 2192638Notes

Reaction equation

HRID 2192638 reaction equation
[Si:1]([O:8][CH:9]1[CH2:14][CH2:13][CH:12]([C:15]2[N:20]=[C:19]([C:21]([O:23]C)=[O:22])[CH:18]=[CH:17][C:16]=2[F:25])[CH2:11][CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[Li+].[OH-].Cl.C(OCC)(=O)C>C1COCC1.CO>[Si:1]([O:8][CH:9]1[CH2:10][CH2:11][CH:12]([C:15]2[N:20]=[C:19]([C:21]([OH:23])=[O:22])[CH:18]=[CH:17][C:16]=2[F:25])[CH2:13][CH2:14]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8857Ethyl AcetateHCID 59226529HCID 59226529, compound

Product 1

HCID 59226525HCID 59226525, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of methyl 6-(4-(tert-butyldimethylsilyloxy)cyclohexyl)-5-fluoropicolinate (1.0 equiv.) in THF/MeOH (2:1, 0.09 M) was added LiOH (1.5 equiv.). The reaction mixture was stirred overnight at room temperature, then 1N HCl and ethyl acetate were added, the organic phase was washed with brine, dried over magnesium sulfate, filtered and concentrated to give 6-(4-(tert-butyldimethylsilyloxy)cyclohexyl)-5-fluoropicolinic acid as a mixture of isomers (3:1) in 82% yield. LC/MS=354.2 (M+H), Rt=1.38 and 1.41 min.

Workup

  1. washthe organic phase was washed with brine
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-ae7beda0b06841528cb750eb1411d22e
Source dataset
uspto-grants-2012_12
Patent number
US08329732B2

Reaction notes

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