Sodium Hydroxide → HCID 58376294, compound

HRID 1942482Notes

Reaction equation

HRID 1942482 reaction equation
[CH2:1]([O:8][C:9]([N:11]([CH:31]([CH3:33])[CH3:32])[C@H:12]1[CH2:17][N:16]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C@@H:15]([CH2:25][C:26]([O:28]CC)=[O:27])[CH2:14][CH2:13]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].S([O-])(O)(=O)=O.[K+]>C(O)C>[CH2:1]([O:8][C:9]([N:11]([CH:31]([CH3:33])[CH3:32])[C@H:12]1[CH2:17][N:16]([C:18]([O:20][C:21]([CH3:23])([CH3:24])[CH3:22])=[O:19])[C@@H:15]([CH2:25][C:26]([OH:28])=[O:27])[CH2:14][CH2:13]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 516920Potassium bisulfateHCID 58376763HCID 58376763, compound

Product 1

HCID 58376294HCID 58376294, compoundYield 75.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of tert-butyl (2R,5R)-5-[[(benzyloxy)carbonyl](isopropyl)amino]-2-(2-ethoxy-2-oxoethyl)piperidine-1-carboxylate (8.5 g) in ethanol (100 mL) was added a 2N aqueous sodium hydroxide solution (50 mL), and the mixture was stirred at 50° C. for one hour. The reaction solution was cooled with ice, and thereto was added an aqueous potassium hydrogen sulfate solution in order to adjust the pH value to pH 3. The mixture was extracted with chloroform, and the organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to give the title compound (6.0 g) as a colorless solid.

Workup

  1. temperatureThe reaction solution was cooled with ice
  2. extractionThe mixture was extracted with chloroform
  3. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-a436307f1b224832b63abb5317c777dd
Source dataset
uspto-grants-2013_03
Patent number
US08389511B2

Reaction notes

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