Hydrochloric Acid → HCID 57966440, compound

HRID 420584Notes

Reaction equation

HRID 420584 reaction equation
C[O:2][C:3](=[O:33])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[C:7]([O:12][CH2:13][CH2:14][C:15]2([CH2:31][CH3:32])[CH2:20][CH2:19][N:18]([C:21]3[S:22][C:23]4[CH:29]=[C:28]([Cl:30])[CH:27]=[CH:26][C:24]=4[N:25]=3)[CH2:17][CH2:16]2)[CH:6]=1.[OH-].[Na+].O1CCCC1.Cl>CO>[Cl:11][C:8]1[CH:9]=[CH:10][C:5]([CH2:4][C:3]([OH:33])=[O:2])=[CH:6][C:7]=1[O:12][CH2:13][CH2:14][C:15]1([CH2:31][CH3:32])[CH2:20][CH2:19][N:18]([C:21]2[S:22][C:23]3[CH:29]=[C:28]([Cl:30])[CH:27]=[CH:26][C:24]=3[N:25]=2)[CH2:17][CH2:16]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 57966630HCID 57966630, compound

Product 1

HCID 57966440HCID 57966440, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of [4-Chloro-3-[2-[1-(6-chlorobenzothiazole-2-yl)-4-ethyl piperidine-4-yl]ethoxy]phenyl]acetic acid methyl ester (152 mg), 2N aqueous sodium hydroxide (0.45 mL), tetrahydrofuran (1 mL) and methanol (1 mL) was stirred at room temperature for 2 hours. The reaction solution was neutralized with 2N hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with water and brine, and dried over sodium sulphate. The solvent was evaporated under reduced pressure and the residue was purified by column chromatograph on silica gel to give the title compound (53 mg). Yield: 36%.

Workup

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

Sources & evidence

ORD record
ord-90720e8e474747519d61d5761a154cf2
Source dataset
uspto-grants-2012_01
Patent number
US08097610B2

Reaction notes

Loading…