Sodium Hydroxide → HCID 11784106, compound

HRID 568111Notes

Reaction equation

HRID 568111 reaction equation
C([O:3][C:4](=[O:30])[CH2:5][N:6]([CH2:28][CH3:29])[C:7](=[O:27])[CH2:8][CH2:9][CH2:10][CH:11]1[CH2:16][CH2:15][N:14]([C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:18])[CH2:13][CH2:12]1)C.[OH-].[Na+]>O1CCCC1>[CH2:28]([N:6]([C:7](=[O:27])[CH2:8][CH2:9][CH2:10][CH:11]1[CH2:16][CH2:15][N:14]([C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:18])[CH2:13][CH2:12]1)[CH2:5][C:4]([OH:30])=[O:3])[CH3:29]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 21263310HCID 21263310, compound

Product 1

HCID 11784106HCID 11784106, compoundYield 81.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 46.7 g (112 mmole) of N-ethyl-N-[1-oxo-4-[1-[(phenylmethoxy)carbonyl]-4-piperidinyl]butyl]glycine ethyl ester in tetrahydrofuran at ambient temperature is added 200 mL of 1N aqueous sodium hydroxide, and the heterogeneous mixture is stirred vigorously for 1 hour. The reaction mixture is concentrated in vacuo and the residual aqueous mixture is diluted with water and extracted with methyl tert-butyl ether (3×). The aqueous layer is acidified to pH 3 with potassium bisulfate, causing an oil to form. The mixture is extracted with methyl tert-butyl ether (3×). The combined organic layers are washed with brine (2×), dried over magnesium sulfate, filtered, and concentrated in vacuo. The resulting oil is subjected to high vacuum to give N-ethyl-N-[1-oxo-4-[1-[(phenylmethoxy)carbonyl]-4-piperidinyl]butyl]glycine (35.5 g). MS (FAB) 391 (M+H)+.

Workup

  1. concentrationThe reaction mixture is concentrated in vacuo
  2. additionthe residual aqueous mixture is diluted with water
  3. extractionextracted with methyl tert-butyl ether (3×)
  4. customto form
  5. extractionThe mixture is extracted with methyl tert-butyl ether (3×)
  6. washThe combined organic layers are washed with brine (2×)
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b6419cde0e1840008d84ece677da1ff5
Source dataset
uspto-grants-2001_01
Patent number
US06180759B2

Reaction notes

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