Hydrochloric Acid → HCID 68501321, compound

HRID 1176429Notes

Reaction equation

HRID 1176429 reaction equation
[CH3:1][O:2][C:3]1[CH:47]=[CH:46][CH:45]=[CH:44][C:4]=1[CH2:5][O:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([CH:17]2[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH:18]2[O:30][CH2:31][CH2:32][O:33]S(C2C=CC(C)=CC=2)(=O)=O)=[CH:13][CH:12]=1.O[C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][C:50]=1[CH2:55][CH2:56][CH2:57][C:58]([OH:60])=[O:59].[OH-].[Na+].Cl>CO.O.C(OCC)(=O)C>[C:58]([CH2:57][CH2:56][CH2:55][C:50]1[CH:51]=[CH:52][CH:53]=[CH:54][C:49]=1[O:33][CH2:32][CH2:31][O:30][CH:18]1[CH:17]([C:14]2[CH:15]=[CH:16][C:11]([O:10][CH2:9][CH2:8][CH2:7][O:6][CH2:5][C:4]3[CH:44]=[CH:45][CH:46]=[CH:47][C:3]=3[O:2][CH3:1])=[CH:12][CH:13]=2)[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:27])([CH3:28])[CH3:29])=[O:24])[CH2:19]1)([OH:60])=[O:59]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 41894984-(2-Hydroxyphenyl)butanoic acidHCID 86609984Tert-butyl 4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}-3-[2-(toluene-4-sulphonyloxy)ethoxy]piperidine-1-carboxylate

Product 1

HCID 68501321HCID 68501321, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Analogously to Method G, 0.549 g of tert-butyl 4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}-3-[2-(toluene-4-sulphonyloxy)ethoxy]piperidine-1-carboxylate (Example 14b) and 0.075 g of 4-(2-hydroxyphenyl)butyric acid are reacted. The yellow oil obtained after chromatography is dissolved in 9.5 ml of methanol and 3.2 ml of water, admixed with 1.5 ml of 1N NaOH and stirred at reflux over 2 hours. The reaction mixture is cooled to room temperature, diluted with ethyl acetate and water and acidified with 2N HCl. The aqueous phase is extracted with ethyl acetate. The combined organic phases are washed with water, dried over sodium sulphate and concentrated by evaporation. The title compound is obtained as a colourless resin from the residue by means of flash chromatography (SiO2 60F). Rf=0.20 (95:5 dichloromethane-methanol); Rt=5.86.

Workup

  1. customThe yellow oil obtained after chromatography
  2. temperatureat reflux over 2 hours
  3. extractionThe aqueous phase is extracted with ethyl acetate
  4. washThe combined organic phases are washed with water
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-97c24b694cac4c448b9941d7666c4b81
Source dataset
uspto-grants-2010_11
Patent number
US07842688B2

Reaction notes

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