Hydrochloric Acid → HCID 14459385, compound

HRID 1904423Notes

Reaction equation

HRID 1904423 reaction equation
CC(C)([O:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][CH2:15]/[C:16](/[CH2:29][N:30]2[CH:34]=[CH:33][N:32]=[CH:31]2)=[CH:17]/[C:18]2[CH:28]=[CH:27][C:21]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:20][CH:19]=2)=[CH:9][CH:8]=1)=[O:6])C.Cl.C(=O)([O-])O.[Na+]>C(O)(=O)C.O>[C:5]([C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][CH2:15]/[C:16](/[CH2:29][N:30]2[CH:34]=[CH:33][N:32]=[CH:31]2)=[CH:17]\[C:18]2[CH:19]=[CH:20][C:21]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:27][CH:28]=2)=[CH:9][CH:8]=1)([OH:6])=[O:4]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 67936292HCID 67936292, compound

Product 1

HCID 14459385HCID 14459385, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A solution containing ethyl 4-[5-[4-[(1,1-dimethylethoxy)carbonyl]phenyl]-2-(1H-imidazol-1-ylmethyl)-1E-pentenyl]benzoate (prepared as in Example 15; 3.5 g, 0.0074 mol) in acetic acid (45 ml) was treated with aqueous hydrochloric acid (5% of 35.4%). The solution was stirred at room temperature for three hours after which time the solution was basified with sodium hydrogen carbonate, diluted with water (500 ml) and extracted with dichloromethane (4×300 ml). The extracts were combined, dried over sodium sulphate, and the solvent was evaporated off under reduced pressure to yield a crude product. The crude product was purified by column chromatography (silica gel, 10% ethanol in chloroform) to yield ethyl 4-[5-(4-carboxyphenyl)-2-(1H-imidazol-1-ylmethyl)1E-pentenyl]benzoate as a colorless crystalline solid having a melting point of 167°-170° C. (chloroform/benzene) and the following structural characteristics:

Workup

  1. extractionextracted with dichloromethane (4×300 ml)
  2. dry with materialdried over sodium sulphate
  3. customthe solvent was evaporated off under reduced pressure
  4. customto yield a crude product
  5. customThe crude product was purified by column chromatography (silica gel, 10% ethanol in chloroform)

Sources & evidence

ORD record
ord-9f2f4aa6e19149abb710d06f500b9fbc
Source dataset
uspto-grants-1989_06
Patent number
US04837333

Reaction notes

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