Lithium Hydroxide → HCID 59715044, compound

HRID 2223889Notes

Reaction equation

HRID 2223889 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]([CH:16]2[CH2:21][CH2:20][N:19]([CH2:22][CH2:23][C:24]3([CH2:30][CH2:31][C:32](C(OCC)=O)([C:38]([O:40]CC)=[O:39])[C:33]([O:35]CC)=[O:34])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]3)[CH2:18][CH2:17]2)[C:9]([C:11]2[O:12][CH:13]=[CH:14][CH:15]=2)=[O:10])=[N:6][CH:7]=1.[OH-].[Li+]>O1CCOCC1.O>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]([CH:16]2[CH2:21][CH2:20][N:19]([CH2:22][CH2:23][C:24]3([CH2:30][CH2:31][CH:32]([C:33]([OH:35])=[O:34])[C:38]([OH:40])=[O:39])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]3)[CH2:18][CH2:17]2)[C:9]([C:11]2[O:12][CH:13]=[CH:14][CH:15]=2)=[O:10])=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 10189806HCID 10189806, compound

Product 1

HCID 59715044HCID 59715044, compoundYield 93.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

To a solution of triethyl 3-[1-[2-[4-[N-(5-methylpyridin-2-yl)-2-furancarboxamido]piperidin-1-yl]ethyl]cyclohexyl]-1,1,1-propanetricarboxylate (200 mg) in 1,4-dioxane (9 mL) and water (3 mL) was added lithium hydroxide (100 mg). After stirring the solution at room temperature for 7 hours, water was added thereto and it was concentrated under reduced pressure. Acetic acid (0.14 mL) was added to the residue, and the solution was further concentrated under reduced pressure and to dryness. The residue was purified by chromatography (DIAION HP20 manufactured by Mitubishi Chemical Corporation, methanol) to give the title compound (150 mg).

Workup

  1. concentrationit was concentrated under reduced pressure
  2. additionAcetic acid (0.14 mL) was added to the residue
  3. concentrationthe solution was further concentrated under reduced pressure and to dryness
  4. customThe residue was purified by chromatography (DIAION HP20 manufactured by Mitubishi Chemical Corporation, methanol)

Sources & evidence

ORD record
ord-5862c18fd9324680817acec26c4d44a1
Source dataset
uspto-grants-2008_05
Patent number
US07375115B2

Reaction notes

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