Lithium Hydroxide → HCID 67056339, compound

HRID 1777272Notes

Reaction equation

HRID 1777272 reaction equation
[OH-].[Li+].[CH2:3]([O:7][C:8]1[CH:28]=[CH:27][C:11]([C:12]([NH:14][CH2:15][C@H:16]([N:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)[C:17]([O:19]C)=[O:18])=[O:13])=[CH:10][CH:9]=1)[C:4]#[C:5][CH3:6]>O1CCCC1>[CH2:3]([O:7][C:8]1[CH:28]=[CH:27][C:11]([C:12]([NH:14][CH2:15][C@H:16]([N:21]2[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]2)[C:17]([OH:19])=[O:18])=[O:13])=[CH:10][CH:9]=1)[C:4]#[C:5][CH3:6]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 86670457HCID 86670457, compound

Product 1

HCID 67056339HCID 67056339, compoundYield 105.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2.5 ml (2.4 mmol) of an aqueous solution of lithium hydroxide having a concentration of 1N are added to a solution of 0.6 g (1.6 mmol) of methyl (S)-3-(4-but-2-ynyloxybenzoylamino)-2-piperidin-1-ylpropanoate in 10 ml of tetrahydrofuran. The reaction medium is then stirred at ambient temperature for 18 h. After evaporating the tetrahydrofuran under vacuum, 2.4 ml of an aqueous solution of hydrochloric acid having a concentration of 1N and water are added then the reaction medium is extracted with ethyl acetate. The organic phase is dried over magnesium sulphate, filtered and concentrated under vacuum. The residue obtained is purified by chromatography over silica gel eluted with a 90/10 dichloromethane/methanol mixture. 580 mg (100%) of (S)-3-(4-but-2-ynyloxybenzoylamino)-2-piperidin-1-ylpropanoic acid are obtained in the form of a white solid.

Workup

  1. customAfter evaporating the tetrahydrofuran under vacuum, 2.4 ml of an aqueous solution of hydrochloric acid having a concentration of 1N and water
  2. additionare added
  3. extractionthe reaction medium is extracted with ethyl acetate
  4. dry with materialThe organic phase is dried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customThe residue obtained
  8. customis purified by chromatography over silica gel
  9. washeluted with a 90/10 dichloromethane/methanol mixture

Sources & evidence

ORD record
ord-4d3c1c3614124c45baebeb5744180824
Source dataset
uspto-grants-2016_02
Patent number
US09266848B2

Reaction notes

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