Acetic Acid → HCID 66574918, compound

HRID 1777364Notes

Reaction equation

HRID 1777364 reaction equation
[OH-].[Na+].[OH-].[K+].C([O:7][C:8]([C:10]1([CH3:40])[CH2:15][CH2:14][N:13]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]3[N:27]=[C:26]([C:28]4[CH:33]=[CH:32][C:31]([CH:34]5[CH2:38][CH2:37][CH2:36][CH2:35]5)=[C:30]([Cl:39])[CH:29]=4)[O:25][N:24]=3)=[CH:19][CH:18]=2)[CH2:12][CH2:11]1)=[O:9])C.C(O)(=O)C>O.O1CCCC1.C(O)C>[Cl:39][C:30]1[CH:29]=[C:28]([C:26]2[O:25][N:24]=[C:23]([C:20]3[CH:19]=[CH:18][C:17]([CH2:16][N:13]4[CH2:12][CH2:11][C:10]([CH3:40])([C:8]([OH:9])=[O:7])[CH2:15][CH2:14]4)=[CH:22][CH:21]=3)[N:27]=2)[CH:33]=[CH:32][C:31]=1[CH:34]1[CH2:38][CH2:37][CH2:36][CH2:35]1

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 14797Potassium HydroxideHCID 14798Sodium HydroxideHCID 70869527HCID 70869527, compound

Product 1

HCID 66574918HCID 66574918, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

A solution of sodium hydroxide (0.13 g, 0.0033 mol) and potassium hydroxide (85% assay, 0.22 g, 0.0033 mol) in demineralized water (5 mL) is added to a solution of 1-{4-[5-(3-chloro-4-cyclopentylphenyl)-[1,2,4]-oxadiazol-3-yl]-benzyl}-4-methylpiperidine-4-carboxylic acid ethyl ester (0.43 g, 0.0008 mol) in a mixture of tetrahydrofuran and ethanol (1:1), 10 ML. The reaction mixture is heated at 80° C. temperature for 3 hrs. It is then concentrated under reduced pressure to give a crude residue which is treated with demineralized water (20 mL) and acidified to pH˜4-5 with 20% aqueous acetic acid solution (10 mL). The resultant solid is filtered, dried and washed with demineralized water (1×20 mL) and acetone (2×5 mL) respectively. Finally it is dried under reduced pressure to get 1-{4-[5-(3-chloro-4-cyclopentylphenyl)-[1,2,4]-oxadiazol-3-yl]-benzyl}-4-methylpiperidine-4-carboxylic acid.

Workup

  1. concentrationIt is then concentrated under reduced pressure
  2. customto give a crude residue which
  3. filtrationThe resultant solid is filtered
  4. customdried
  5. washwashed with demineralized water (1×20 mL) and acetone (2×5 mL) respectively
  6. customFinally it is dried under reduced pressure

Sources & evidence

ORD record
ord-bb82652c9f93437d80a85da83860c7e1
Source dataset
uspto-grants-2016_02
Patent number
US09266867B2

Reaction notes

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