Potassium Hydroxide → HCID 66574520, compound

HRID 1777366Notes

Reaction equation

HRID 1777366 reaction equation
[OH-].[K+].C1OCCOCCOCCOCCOCCOC1.C([O:23][C:24]([C:26]1([CH2:56][O:57][CH3:58])[CH2:31][CH2:30][N:29]([CH2:32][C:33]2[CH:38]=[CH:37][C:36]([C:39]3[N:43]=[C:42]([C:44]4[CH:49]=[CH:48][C:47]([CH:50]5[CH2:54][CH2:53][CH2:52][CH2:51]5)=[C:46]([Cl:55])[CH:45]=4)[O:41][N:40]=3)=[CH:35][CH:34]=2)[CH2:28][CH2:27]1)=[O:25])C>C1(C)C=CC=CC=1>[Cl:55][C:46]1[CH:45]=[C:44]([C:42]2[O:41][N:40]=[C:39]([C:36]3[CH:37]=[CH:38][C:33]([CH2:32][N:29]4[CH2:30][CH2:31][C:26]([CH2:56][O:57][CH3:58])([C:24]([OH:25])=[O:23])[CH2:27][CH2:28]4)=[CH:34][CH:35]=3)[N:43]=2)[CH:49]=[CH:48][C:47]=1[CH:50]1[CH2:51][CH2:52][CH2:53][CH2:54]1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 2855718-Crown-6HCID 70869460HCID 70869460, compound

Product 1

HCID 66574520HCID 66574520, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Potassium hydroxide powder (85% assay, 0.32 g, 0.0049 mol) and 18-crown-6-ether (0.01 g) are added to a solution of 1-{4-[5-(3-chloro-4-cyclopentylphenyl)-[1,2,4]-oxadiazol-3-yl]benzyl}-4-methoxymethylpiperidine-4-carboxylic acid ethyl ester (0.3 g, 0.00056 mol) in dry toluene (15 mL). The reaction mixture is refluxed for 3 hrs. It is then concentrated under reduced pressure and the residue is acidified to pH˜4-5 with 20% aqueous solution of acetic acid (10 mL). The precipitated solid is filtered, dried and washed with demineralised water (2×10 mL) and acetone (2×5 mL). Solid mass is dissolved in a solution of methanol:dichlromethane:t-butylamine (1:8.9:0.1; 5 mL) and concentrated under reduced pressure to get crude residue which is purified by column chromatography (silica gel 230-400 mesh, methanol:dichloromethane:t-butylamine, 1:8.9:0.1) to give 1-{4-[5-(3-chloro-4-cyclopentylphenyl)-[1,2,4]-oxadiazol-3-yl]benzyl}-4-methoxymethylpiperidine-4-carboxylic acid.

Workup

  1. temperatureThe reaction mixture is refluxed for 3 hrs
  2. concentrationIt is then concentrated under reduced pressure
  3. filtrationThe precipitated solid is filtered
  4. customdried
  5. washwashed with demineralised water (2×10 mL) and acetone (2×5 mL)
  6. dissolutionSolid mass is dissolved in a solution of methanol
  7. concentrationdichlromethane:t-butylamine (1:8.9:0.1; 5 mL) and concentrated under reduced pressure
  8. customto get crude residue which
  9. customis purified by column chromatography (silica gel 230-400 mesh, methanol:dichloromethane:t-butylamine, 1:8.9:0.1)

Sources & evidence

ORD record
ord-fa5d5319f809431d9797a6113c3d934e
Source dataset
uspto-grants-2016_02
Patent number
US09266867B2

Reaction notes

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