Hydrochloric Acid → HCID 23138961, compound

HRID 1171660Notes

Reaction equation

HRID 1171660 reaction equation
[ClH:1].[CH:2]1([C:5](=[O:33])[CH:6]([N:14]2[CH2:19][CH2:18][CH:17]([SH:20])/[C:16](=[CH:21]/[C:22]3[N:23]=[CH:24][N:25]([CH2:27][C:28]([O:30]CC)=[O:29])[CH:26]=3)/[CH2:15]2)[C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[F:13])[CH2:4][CH2:3]1.O1CCCC1.[OH-].[Na+].Cl>O>[ClH:1].[C:28]([CH2:27][N:25]1[CH:26]=[C:22](/[CH:21]=[C:16]2\[CH2:15][N:14]([CH:6]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[F:13])[C:5]([CH:2]3[CH2:3][CH2:4]3)=[O:33])[CH2:19][CH2:18][CH:17]\2[SH:20])[N:23]=[CH:24]1)([OH:30])=[O:29]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 23138797HCID 23138797, compound

Product 1

HCID 23138961HCID 23138961, compoundYield 80.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of (E)-1-[2-cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl]-3-{[1-(ethoxycarbonylmethyl)-1H-imidazol-4-yl]methylidene}-4-sulfanylpiperidine hydrochloride (72.6 mg) in a mixed solvent of tetrahydrofuran (2 ml) and water (1 ml) was added 1N aqueous sodium hydroxide solution (0.55 ml) with stirring under ice-cooling, and the resulting mixture was stirred at the same temperature for 3 minutes. To the reaction mixture was added 1N hydrochloric acid solution (1.00 ml). The reaction mixture was concentrated in vacuo, and the residue was purified by chromatography on a silica gel column using a mixed solvent of methanol and dichloromethane (1:4) as the eluent to afford the title compound (55.4 mg, yield: 80%) as a pale yellow solid.

Workup

  1. temperaturecooling
  2. stirringthe resulting mixture was stirred at the same temperature for 3 minutes
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. customthe residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-2eb4cd143f884e8692e593be20403fdf
Source dataset
uspto-grants-2010_11
Patent number
US07829580B2

Reaction notes

Loading…