Hydrochloric Acid → HCID 86758313, compound

HRID 2228002Notes

Reaction equation

HRID 2228002 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH2:20][CH2:21][N:22]2[CH:26]=[CH:25][N:24]=[CH:23]2)=[CH:9][C:10]2[CH:11]=[C:12]([CH:17]=[CH:18][CH:19]=2)[C:13]([O:15]C)=[O:14])=[CH:4][CH:3]=1.[OH-].[Na+].Cl>CO>[F:1][C:2]1[CH:7]=[CH:6][C:5](/[C:8](/[CH2:20][CH2:21][N:22]2[CH:26]=[CH:25][N:24]=[CH:23]2)=[CH:9]\[C:10]2[CH:11]=[C:12]([CH:17]=[CH:18][CH:19]=2)[C:13]([OH:15])=[O:14])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 54195630HCID 54195630, compound

Product 1

HCID 86758313HCID 86758313, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of Z isomer product from step D (0.64 g, 1.83 mmol) in MeOH (2 ml) was treated with 1N NaOH (2 ml). The resulting suspension was stirred at room temperature for 20 hrs and the acidity adjusted to pH 5 with 1N HCl. The solution was evaporated to dryness and the residue purified by chromatography isolute column (10 g, SiO2) with an eluent of dichloromethane/MeOH (9:1) to give 3-[(Z)-2-(4-fluorophenyl)-4-(imidazol-1-yl)-but-1-enyl]-benzoic acid 0.56 g, (91%) as a white solid.

Workup

  1. customThe solution was evaporated to dryness
  2. customthe residue purified by chromatography isolute column (10 g, SiO2) with an eluent of dichloromethane/MeOH (9:1)

Sources & evidence

ORD record
ord-89c8e3a1f75847bf9003e496cc7fe7ba
Source dataset
uspto-grants-2002_07
Patent number
US06414145B1

Reaction notes

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