Hydrochloric Acid → HCID 53742729, compound

HRID 481293Notes

Reaction equation

HRID 481293 reaction equation
[CH3:1][C@@H:2]1[CH2:7][NH:6][C@H:5]([C:8]([OH:10])=[O:9])[CH2:4][CH2:3]1.C(=O)([O-])O.[Na+].[C:16](OC(=O)C)(=[O:18])[CH3:17].Cl>ClCCl.O>[C:16]([N:6]1[CH2:7][C@@H:2]([CH3:1])[CH2:3][CH2:4][C@H:5]1[C:8]([OH:10])=[O:9])(=[O:18])[CH3:17]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 57108817HCID 57108817, compound

Product 1

HCID 53742729HCID 53742729, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 21908982Water methylene chlorideSolvent

Procedure

15.9 g (111 mmol) of the (2S*,5S*)-5-methylpiperidine-2-carboxylic acid described above was dissolved in 220 ml of a dichloromethane/water (1:1). 93.3 g (1.11 mol) of sodium hydrogencarbonate and 21.0 ml (222 mmol) of acetic anhydride were added thereto in this order at room temperature, followed by stirring for 3 days. The reaction solution was poured into 6N-hydrochloric acid under cooling with ice, and the extraction with chloroform was conducted. Then, the organic layer was dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated in a reduced pressure to give 20.1 g of the title compound as a colorless oil. Yield 98%.

Workup

  1. customat room temperature
  2. temperatureunder cooling with ice
  3. extractionthe extraction with chloroform
  4. dry with materialThen, the organic layer was dried over anhydrous sodium sulfate
  5. filtrationAfter filtration
  6. concentrationthe filtrate was concentrated in a reduced pressure

Sources & evidence

ORD record
ord-01e78806deac4ab193ac740e3be59e49
Source dataset
uspto-grants-1998_08
Patent number
US05789403

Reaction notes

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