Potassium Hydroxide → 5-(benzyloxy)-4-fluoro-2-(tetrahydro-2H-pyran-4-ylamino)benzoic acid

HRID 1022484Notes

Reaction equation

HRID 1022484 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([F:27])=[CH:11][C:12]([NH:20][CH:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)=[C:13]([CH:19]=1)[C:14]([O:16]CC)=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+]>C(O)(C)C.O>[CH2:1]([O:8][C:9]1[C:10]([F:27])=[CH:11][C:12]([NH:20][CH:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)=[C:13]([CH:19]=1)[C:14]([OH:16])=[O:15])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 67495078ethyl 5-(benzyloxy)-4-fluoro-2-(tetrahydro-2H-pyran-4-ylamino)benzoate

Product 1

HCID 667327195-(benzyloxy)-4-fluoro-2-(tetrahydro-2H-pyran-4-ylamino)benzoic acidYield 98.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

A mixture of 1.0 g of the compound obtained in Step 4.3 and 0.45 g of KOH in 16 ml of isopropanol and 4 ml of water is irradiated in a microwave field for 20 minutes at 130° C. The reaction medium is evaporated under reduced pressure. Water is added, the resulting mixture is acidified with aqueous 1N HCl solution to pH 3 and this mixture is extracted with EtOAc. The organic phase is dried over Na2SO4 and filtered, and the filtrate is evaporated under reduced pressure to give 0.91 g of the expected product.

Workup

  1. customis irradiated in a microwave field for 20 minutes at 130° C
  2. customThe reaction medium is evaporated under reduced pressure
  3. additionWater is added
  4. extractionthis mixture is extracted with EtOAc
  5. dry with materialThe organic phase is dried over Na2SO4
  6. filtrationfiltered
  7. customthe filtrate is evaporated under reduced pressure

Sources & evidence

ORD record
ord-47b0961239a242378467d8eac3416d51
Source dataset
uspto-grants-2014_05
Patent number
US08722659B2

Reaction notes

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