Hydrochloric Acid → HCID 59714877, compound

HRID 2223917Notes

Reaction equation

HRID 2223917 reaction equation
[C:1]1([CH3:42])[CH:6]=[CH:5][C:4]([N:7]([CH:15]2[CH2:20][CH2:19][N:18]([CH2:21][CH2:22][C:23]3([CH2:29][CH2:30][O:31][C:32]4[CH:41]=[CH:40][CH:39]=[CH:38][C:33]=4[C:34]([O:36]C)=[O:35])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]3)[CH2:17][CH2:16]2)[C:8]([C:10]2[O:11][CH:12]=[CH:13][CH:14]=2)=[O:9])=[CH:3][CH:2]=1.[OH-].[Na+].Cl>CO.O>[C:1]1([CH3:42])[CH:2]=[CH:3][C:4]([N:7]([CH:15]2[CH2:20][CH2:19][N:18]([CH2:21][CH2:22][C:23]3([CH2:29][CH2:30][O:31][C:32]4[CH:41]=[CH:40][CH:39]=[CH:38][C:33]=4[C:34]([OH:36])=[O:35])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]3)[CH2:17][CH2:16]2)[C:8]([C:10]2[O:11][CH:12]=[CH:13][CH:14]=2)=[O:9])=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59715040HCID 59715040, compound

Product 1

HCID 59714877HCID 59714877, compoundYield 79.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of methyl 2-[2-[1-[2-[4-[N-(p-tolyl)-2-furancarboxamido]piperidin-1-yl]ethyl]cyclohexyl]ethoxy]benzoate (synthesized in Example 39) (221 mg) in methanol (5 mL) was added a sodium hydroxide (77 mg) solution in water (3 mL) dropwise at room temperature. The solution was stirred for 18 hours. After neutralizing the reaction solution with 2N hydrochloric acid, silica gel was added to the solution. The solution was concentrated under reduced pressure. The resulting residue was purified by chromatography [silica gel, chloroform-methanol (10:1)] to give the title compound (172 mg).

Workup

  1. additionwas added to the solution
  2. concentrationThe solution was concentrated under reduced pressure
  3. customThe resulting residue was purified by chromatography [silica gel, chloroform-methanol (10:1)]

Sources & evidence

ORD record
ord-90ad1b5a49f04813a6dc9c1f674c366e
Source dataset
uspto-grants-2008_05
Patent number
US07375115B2

Reaction notes

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