Hydrochloric Acid → HCID 131722857, compound

HRID 1596705Notes

Reaction equation

HRID 1596705 reaction equation
[CH2:1]([N:3]([CH2:29][CH3:30])[C:4]([CH:6]=[C:7]([C:9]1[CH:10]=[CH:11][C:12]([O:20][CH:21]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH3:22])=[C:13]([CH:19]=1)[O:14][CH2:15][C:16]([OH:18])=[O:17])[CH3:8])=[O:5])[CH3:2].[CH:31](O)([CH3:33])[CH3:32].Cl>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH2:29]([N:3]([CH2:1][CH3:2])[C:4](/[CH:6]=[C:7](/[C:9]1[CH:10]=[CH:11][C:12]([O:20][CH:21]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH3:22])=[C:13]([CH:19]=1)[O:14][CH2:15][C:16]([O:18][CH:31]([CH3:33])[CH3:32])=[O:17])\[CH3:8])=[O:5])[CH3:30]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3776IsopropanolHCID 54243972HCID 54243972, compound

Product 1

HCID 131722857HCID 131722857, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of [5-(2-diethycarbamoyl-1-methylvinyl)-2-(1-phenylethoxy)-phenoxy]-acetic acid (300 mg, 0.97 mmol), 4-dimethylaminopyridine (12 mg, 0.097 mmol) and isopropanol (117 mg, 1.95 mmol) in methylene chloride (30 mL) is cooled to 0° C., and 1-(3-dimethylaminopropyl)-3-etbylcarbodiimide.HCl (205 mg, 1.07 mmol) is added in one portion. The mixture is then allowed to stir at room temperature for 18 hours. After washing with water (50 ml), the organic layer is washed with saturated NaHCO3 (50 mL) and brine (50 mL), dried over Na2SO4 and concentrated in vacuo. Chromatography (silica, 1:1 EtOAc/hexane) yields isopropyl (E)-[5-(2-diethylcarbamoyl-1-methylvinyl)-2-(1-phenylethoxy)-phenoxy]-acetate MS: 454 (M++1), 350 (M+-PhCHCH3+).

Workup

  1. washAfter washing with water (50 ml)
  2. washthe organic layer is washed with saturated NaHCO3 (50 mL) and brine (50 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-437c1eba4d5a4ca39922cc32dd16c3d0
Source dataset
uspto-grants-2001_09
Patent number
US06291530B1

Reaction notes

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