Hydrochloric Acid → HCID 68502699, compound

HRID 1712345Notes

Reaction equation

HRID 1712345 reaction equation
C[C:2]1[C:3]([O:39][CH2:40][CH2:41][CH2:42][O:43][CH3:44])=[C:4]([CH:8]=[CH:9][C:10]=1[CH2:11][O:12][CH:13]1[CH:18]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH2:27][CH2:28][O:29][CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=3[O:37][CH3:38])=[CH:21][CH:20]=2)[CH2:17][CH2:16][NH:15][CH2:14]1)[C:5]([OH:7])=[O:6].[OH-].[Na+].Cl>CO>[CH3:38][O:37][C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=1[CH2:30][O:29][CH2:28][CH2:27][CH2:26][O:25][C:22]1[CH:21]=[CH:20][C:19]([CH:18]2[CH2:17][CH2:16][NH:15][CH2:14][CH:13]2[O:12][CH2:11][C:10]2[CH:9]=[CH:8][C:4]([C:5]([OH:7])=[O:6])=[C:3]([O:39][CH2:40][CH2:41][CH2:42][O:43][CH3:44])[CH:2]=2)=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 68503158HCID 68503158, compound

Product 1

HCID 68502699HCID 68502699, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

The solution of 0.025 g of methyl 4-(4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}piperidin-3-yloxymethyl)-2-(3-methoxypropoxy)benzoic acid (Example 29) in 0.200 ml of methanol is admixed with 0.200 ml of 1M NaOH and stirred at 65° C. over 1 hour. The reaction mixture is cooled, admixed with 0.100 ml of 2M HCl and extracted with ethyl acetate (3×2 ml). The organic phases are concentrated by evaporation. The title compound is obtained as a slightly yellowish oil from the residue by means of flash chromatography (SiO2 60F). Rf=0.19 (750:270:50:5 dichloromethane-methanol-water-AcOH); Rt=4.08.

Workup

  1. temperatureThe reaction mixture is cooled
  2. extractionextracted with ethyl acetate (3×2 ml)
  3. concentrationThe organic phases are concentrated by evaporation

Sources & evidence

ORD record
ord-4b179c2fe12846c8872fc6374eaea964
Source dataset
uspto-grants-2010_09
Patent number
US07790715B2

Reaction notes

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