Methanol → [3-[2-[1-(5-Bromothiazole-2-yl)-4-pyrrolidine-1-ylpiperidine-4-yl]ethoxy]-5-chlorophenyl]acetic acid

HRID 420601Notes

Reaction equation

HRID 420601 reaction equation
C[O:2][C:3](=[O:32])[CH2:4][C:5]1[CH:10]=[C:9]([Cl:11])[CH:8]=[C:7]([O:12][CH2:13][CH2:14][C:15]2([N:27]3[CH2:31][CH2:30][CH2:29][CH2:28]3)[CH2:20][CH2:19][N:18]([C:21]3[S:22][C:23]([Br:26])=[CH:24][N:25]=3)[CH2:17][CH2:16]2)[CH:6]=1.[OH-].[Na+].O1CCCC1.CO>O>[Br:26][C:23]1[S:22][C:21]([N:18]2[CH2:19][CH2:20][C:15]([CH2:14][CH2:13][O:12][C:7]3[CH:6]=[C:5]([CH2:4][C:3]([OH:32])=[O:2])[CH:10]=[C:9]([Cl:11])[CH:8]=3)([N:27]3[CH2:28][CH2:29][CH2:30][CH2:31]3)[CH2:16][CH2:17]2)=[N:25][CH:24]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 66657791[3-[2-[1-(5-Bromothiazole-2-yl)-4-pyrrolidine-1-ylpiperidine-4-yl]ethoxy]-5-chlorophenyl]acetic acid methyl ester

Product 1

HCID 66657808[3-[2-[1-(5-Bromothiazole-2-yl)-4-pyrrolidine-1-ylpiperidine-4-yl]ethoxy]-5-chlorophenyl]acetic acidYield 65%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of [3-[2-[1-(5-bromothiazole-2-yl)-4-pyrrolidine-1-ylpiperidine-4-yl]ethoxy]-5-chlorophenyl]acetic acid methyl ester (1.45 g), 2N sodium hydroxide (3.3 mL), tetrahydrofuran (15 mL) and methanol (15 mL) was stirred at room temperature for 3 hours. To the reaction solution was added water and washed with chloroform. The water layer was neutralized with 2N hydrochloric acid and extracted with chloroform. The organic layer was washed with water and brine, and dried over magnesium sulphate. The solvent was evaporated under reduced pressure and the residue was purified by column chromatograph on silica gel to give the title compound (916 mg). Yield: 65%.

Workup

  1. washwashed with chloroform
  2. extractionextracted with chloroform
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over magnesium sulphate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by column chromatograph on silica gel

Sources & evidence

ORD record
ord-8fb19bad68a74afabdfd1ae88b1d82af
Source dataset
uspto-grants-2012_01
Patent number
US08097610B2

Reaction notes

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