Lithium hydroxide, monohydrate → HCID 86700858, compound

HRID 881753Notes

Reaction equation

HRID 881753 reaction equation
C[O:2][C:3](=[O:35])[CH2:4][C:5]12[CH2:12][CH2:11][C:8]([C:13]3[CH:18]=[CH:17][C:16]([C:19]4[CH:24]=[CH:23][C:22]([NH:25][C:26]5[O:27][C:28]([C:31]([CH3:34])([CH3:33])[CH3:32])=[N:29][N:30]=5)=[CH:21][CH:20]=4)=[CH:15][CH:14]=3)([CH2:9][CH2:10]1)[O:7][CH2:6]2.O.[OH-].[Li+]>O1CCCC1.C(O)C.O>[C:31]([C:28]1[O:27][C:26]([NH:25][C:22]2[CH:21]=[CH:20][C:19]([C:16]3[CH:17]=[CH:18][C:13]([C:8]45[CH2:9][CH2:10][C:5]([CH2:4][C:3]([OH:35])=[O:2])([CH2:12][CH2:11]4)[CH2:6][O:7]5)=[CH:14][CH:15]=3)=[CH:24][CH:23]=2)=[N:30][N:29]=1)([CH3:34])([CH3:32])[CH3:33]

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 86700856HCID 86700856, compound

Product 1

HCID 86700858HCID 86700858, compoundYield 71.6%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

A 100 ml round bottom flask was charged with {1-[4′-(5-tert-butyl-[1,3,4]oxadiazol-2-ylamino)-biphenyl-4-yl]-2-oxa-bicyclo[2.2.2]oct-4-yl}-acetic acid methyl ester (0.27 g, 0.454 mmol), and lithium hydroxide monohydrate (0.229 g, 5.45 mmol) in tetrahydrofuran (20 ml), ethanol (10 ml) and water (8 ml) at room temperature. The mixture was heated at 50° C. for 2 hours. Most of the organic solvent was evaporated under vacuum and the mixture was acidified to PH=4 at 0° C. The solvents were then removed by lipherlizer. The mixture was added ethanol (40 ml) and heated to 70° C., and then was cooled to room temperature. The mixture was filtered and the solid was washed with ethanol (3 ml) and water (10 ml) to afford {1-[4′-(5-tert-butyl-[1,3,4]oxadiazol-2-ylamino)-biphenyl-4-yl]-2-oxa-bicyclo[2.2.2]oct-4-yl}-acetic acid (150 mg, 71%) as white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.64-1.89 (m, 6H) 2.00-2.13 (m, 4H) 3.85 (s, 2H) 7.42 (d, J=8.40 Hz, 2H) 7.55 (d, J=8.50 Hz, 2H) 7.62 (s, 4H) 10.46 (br. s, 1H). LC/MS, [MS+] 461.23, RT: 2.66 (Condition M).

Workup

  1. customMost of the organic solvent was evaporated under vacuum
  2. customat 0° C
  3. customThe solvents were then removed by lipherlizer
  4. additionThe mixture was added ethanol (40 ml)
  5. temperatureheated to 70° C.
  6. temperaturewas cooled to room temperature
  7. filtrationThe mixture was filtered
  8. washthe solid was washed with ethanol (3 ml) and water (10 ml)

Sources & evidence

ORD record
ord-9f44fda6f32e4dd18d62bf412400513b
Source dataset
uspto-grants-2015_03
Patent number
US08993619B2

Reaction notes

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