Methanol → 3-(4,5,7-Trifluorobenzothiazol-2-yl)propionic acid

HRID 1940609

Reaction equation

HRID 1940609 reaction equation
CO.[OH-].[Na+].[F:5][C:6]1[C:11]2[N:12]=[C:13]([CH2:15][CH2:16][C:17]([O:19]CC)=[O:18])[S:14][C:10]=2[C:9]([F:22])=[CH:8][C:7]=1[F:23]>O>[F:5][C:6]1[C:11]2[N:12]=[C:13]([CH2:15][CH2:16][C:17]([OH:19])=[O:18])[S:14][C:10]=2[C:9]([F:22])=[CH:8][C:7]=1[F:23]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 21463563Ethyl 3-(4,5,7-trifluorobenzothiazol-2-yl)propionate

Product 1

HCID 214635293-(4,5,7-Trifluorobenzothiazol-2-yl)propionic acidYield 85%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a mixture of methanol (8 ml), water (6 ml) and 2N sodium hydroxide (2 ml, 4 mmol) was added ethyl 3-(4,5,7-trifluorobenzothiazol-2-yl)propionate (1.1 g, 3.8 mmol) and the mixture was stirred for 15 min. at ambient temperature. The reaction solution was diluted with water and then extracted with ethyl acetate. The organic layer was washed with water, then dried and evaporated to yield a residue, which was recrystallized from hexane-isopropyl ether to give 3-(4,5,7-trifluorobenzothiazol-2-yl)propionic acid (840 mg, 85%) as colorless needles.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. customdried
  4. customevaporated
  5. customto yield a residue, which
  6. customwas recrystallized from hexane-isopropyl ether

Sources & evidence

ORD record
ord-ce24b89938924a28b11bba22ecc063e1
Source dataset
uspto-grants-1997_12
Patent number
US05700819

Linked notes

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