Sodium Hydroxide → HCID 58297268, compound

HRID 538636Notes

Reaction equation

HRID 538636 reaction equation
C([O:3][C:4](=[O:20])[C:5]([N:8]([CH:10]1[CH2:15][CH2:14][N:13]([S:16]([CH3:19])(=[O:18])=[O:17])[CH2:12][CH2:11]1)[CH3:9])([CH3:7])[CH3:6])C.[OH-].[Na+]>CCO>[CH3:19][S:16]([N:13]1[CH2:14][CH2:15][CH:10]([N:8]([CH3:9])[C:5]([CH3:6])([CH3:7])[C:4]([OH:20])=[O:3])[CH2:11][CH2:12]1)(=[O:18])=[O:17]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58297302HCID 58297302, compound

Product 1

HCID 58297268HCID 58297268, compoundYield 37.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

0.76 g (2.48 mmol) of 2-[(1-methanesulfonyl-piperidin-4-yl)-methyl-amino]-2-methyl-propionic acid ethyl ester are dissolved in EtOH (14.3 mL) and 3.72 mL (14.9 mmol) 4 N NaOH are added at RT. The reaction is refluxed for 16 h. The solvent is removed under reduced pressure, the residue is diluted with water and neutralized to pH 7 and lyophilized. The product is dissolved in acetone and filtered. The solvent is removed under reduced pressure to afford 0.26 g of 2-[(1-methanesulfonyl-piperidin-4-yl)-methyl-amino]-2-methyl-propionic acid. Yield: 37%; ESI-MS: 279 [M+H]+; HPLC (Rt): 0.23 min (method D)

Workup

  1. temperatureThe reaction is refluxed for 16 h
  2. customThe solvent is removed under reduced pressure
  3. additionthe residue is diluted with water and neutralized to pH 7
  4. dissolutionThe product is dissolved in acetone
  5. filtrationfiltered
  6. customThe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-fe17079b977e47be9d80e72f72008c44
Source dataset
uspto-grants-2014_10
Patent number
US08865744B1

Reaction notes

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