Water → HCID 178525699, compound

HRID 221339Notes

Reaction equation

HRID 221339 reaction equation
O.[OH-].[Li+].C[O:5][C:6]([CH:8]1[CH2:13][CH2:12][CH:11]([C:14]2[O:18][N:17]=[C:16]([C:19]3[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=3)[N:15]=2)[CH2:10][CH2:9]1)=[O:7]>C1COCC1>[N:22]1[CH:23]=[CH:24][C:19]([C:16]2[N:15]=[C:14]([C@H:11]3[CH2:10][CH2:9][C@H:8]([C:6]([OH:7])=[O:5])[CH2:13][CH2:12]3)[O:18][N:17]=2)=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 57954377HCID 57954377, compound

Product 1

HCID 178525699HCID 178525699, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

Water (0.5 ml) and lithium hydroxide (9.2 mg, 0.22 mmol) were added to a stirred solution of 4-(3-pyridin-4-yl-[1,2,4]oxadiazol-5-yl)cyclohexanecarboxylic acid methyl ester (Preparation 3, 30 mg, 104 μmol) in THF (1.5 ml). The mixture was heated at 60° C. for 1.5 h, cooled and the THF removed in vacuo. Water (5 ml) was added, the aqueous washed with EtOAc (5 ml) and carefully acidified with 1M HCl to pH 4. The resulting precipitate was extracted into 3% MeOH in EtOAc (2×15 ml) and the combined organic phases dried (MgSO4) and evaporated to afford the title compound: RT=2.74 min, m/z (ES+)=274.2 [M+H]+.

Workup

  1. temperaturecooled
  2. customthe THF removed in vacuo
  3. additionWater (5 ml) was added
  4. washthe aqueous washed with EtOAc (5 ml)
  5. extractionThe resulting precipitate was extracted into 3% MeOH in EtOAc (2×15 ml)
  6. dry with materialthe combined organic phases dried (MgSO4)
  7. customevaporated

Sources & evidence

ORD record
ord-89953ac92c40487bbf2b05f5963ee9b6
Source dataset
uspto-grants-2012_06
Patent number
US08207147B2

Reaction notes

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