Lithium Hydroxide → HCID 66667042, compound

HRID 1617980Notes

Reaction equation

HRID 1617980 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8](=[O:38])[CH2:9][C@H:10]([C:18]2[CH:23]=[CH:22][C:21]([N:24]3[CH2:29][CH2:28][CH:27]([C:30]([NH:32][CH2:33][C:34]([O:36]C)=[O:35])=[O:31])[CH2:26][CH2:25]3)=[CH:20][CH:19]=2)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[CH3:17])[CH:5]=[CH:4][N:3]=1.[OH-].[Li+].S([O-])(O)(=O)=O.[K+].[Cl-].[NH4+]>O1CCCC1.CO>[CH3:1][C:2]1[CH:7]=[C:6]([C:8](=[O:38])[CH2:9][C@H:10]([C:18]2[CH:23]=[CH:22][C:21]([N:24]3[CH2:25][CH2:26][CH:27]([C:30]([NH:32][CH2:33][C:34]([OH:36])=[O:35])=[O:31])[CH2:28][CH2:29]3)=[CH:20][CH:19]=2)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[CH3:17])[CH:5]=[CH:4][N:3]=1

Participants

7

Reactant 4

HCID 3939Lithium HydroxideHCID 25517Ammonium ChlorideHCID 516920Potassium bisulfateHCID 66666644HCID 66666644, compound

Product 1

HCID 66667042HCID 66667042, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of (R)-methyl 2-(1-(4-(3-(2-methylpyridin-4-yl)-3-oxo-1-o-tolylpropyl)-phenyl)piperidine-4-carboxamido)acetate (116 mg, 226 μmol) in tetrahydrofuran (3 mL), 1 M aq. lithium hydroxide solution (2.26 mL, 2.26 mmol) and methanol (1 mL) was stirred for 2 h at room temperature, then after addition of 1 M aq. potassium hydrogensulfate solution (2.5 mL) and sat. aq. ammonium chloride solution (5 mL) the reaction mixture was extracted with ethyl acetate. The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo to produce [(1-{4-[(R)-3-(2-methyl-pyridin-4-yl)-3-oxo-1-o-tolyl-propyl]-phenyl}-piperidine-4-carbonyl)-amino]-acetic acid. This was reacted in analogy to example 132, step 6 with hydroxylamine hydrochloride in the presence of sodium hydrogencarbonate to produce the title compound (42 mg, 36%). Yellow semisolid, MS (ESI+): m/z=515.6 ([M+H]+).

Workup

  1. extractionwas extracted with ethyl acetate
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fc3022f4b792467c9c7422d6007fb71a
Source dataset
uspto-grants-2014_07
Patent number
US08765730B2

Reaction notes

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