Sodium Hydroxide → 2-{3-[2-(Trifluoromethyl)phenoxy]pyrrolidin-1-yl}-1,3-thiazole-5-carboxylic acid

HRID 2355059Notes

Reaction equation

HRID 2355059 reaction equation
[F:1][C:2]([F:25])([F:24])[C:3]1[CH:23]=[CH:22][CH:21]=[CH:20][C:4]=1[O:5][CH:6]1[CH2:10][CH2:9][N:8]([C:11]2[S:12][C:13]([C:16]([O:18]C)=[O:17])=[CH:14][N:15]=2)[CH2:7]1.[OH-].[Na+]>C1COCC1.CO>[F:24][C:2]([F:1])([F:25])[C:3]1[CH:23]=[CH:22][CH:21]=[CH:20][C:4]=1[O:5][CH:6]1[CH2:10][CH2:9][N:8]([C:11]2[S:12][C:13]([C:16]([OH:18])=[O:17])=[CH:14][N:15]=2)[CH2:7]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68452698Methyl 2-{3-[2-(trifluoromethyl)phenoxy]pyrrolidin-1-yl}-1,3-thiazole-5-carboxylate

Product 1

HCID 684517792-{3-[2-(Trifluoromethyl)phenoxy]pyrrolidin-1-yl}-1,3-thiazole-5-carboxylic acid

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of methyl 2-{3-[2-(trifluoromethyl)phenoxy]pyrrolidin-1-yl}-1,3-thiazole-5-carboxylate (1.2 g, 3.2 mmol) and 1M aqueous NaOH (6.4 mL, 6.4 mmol) in THF-MeOH (1:1, 24 mL) was heated at 80° C. bath for 2 h. Volatile solvents were removed in vacuo. The residue was diluted with H2O, acidified with 1M HCl (7 mL) and extracted with EtOAc. The EtOAc extract was washed with H2O, dried (Na2SO4), concentrated and triturated with Et2O to give the title compound as white solid. 1H NMR (400 MHz, acetone-d6): δ 7.84 (s, 1 H), 7.67 (m, 2 H), 7.41 (d, 1 H), 7.17 (t, 1 H), 5.51 (s, 1 H), 3.95 (m, 1 H), 3.81-3.60 (m, 3 H), 2.60-2.40 (m, 2 H).

Workup

  1. customVolatile solvents were removed in vacuo
  2. additionThe residue was diluted with H2O
  3. extractionextracted with EtOAc
  4. extractionThe EtOAc extract
  5. washwas washed with H2O
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated
  8. customtriturated with Et2O

Sources & evidence

ORD record
ord-8a572a0e42614b9c9b189786c2f82402
Source dataset
uspto-grants-2010_07
Patent number
US07754745B2

Reaction notes

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