Cycloleucine → 1-[(Ethoxycarbonyl)amino]cyclopentane-1-carboxylic acid

HRID 484386Notes

Reaction equation

HRID 484386 reaction equation
[NH2:1][C:2]1([C:7]([OH:9])=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3]1.C(=O)(O)[O-].[Na+].Cl[C:16]([O:18][CH2:19][CH3:20])=[O:17]>C(OCC)C>[CH2:19]([O:18][C:16]([NH:1][C:2]1([C:7]([OH:9])=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3]1)=[O:17])[CH3:20]

Participants

5

Reactant 3

HCID 2901CycloleucineHCID 10928Ethyl chloroformateHCID 516892Sodium Bicarbonate

Product 1

HCID 197480841-[(Ethoxycarbonyl)amino]cyclopentane-1-carboxylic acid

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To an aqueous solution (35 ml) of 1-amino-1-carboxycyclopentane (1.29 g; 10 mmol) and sodium bicarbonate (1.85 g; 22 mmol), a solution of ethyl chloroformate (1.30 g; 12 mmol) in diethyl ether (10 ml) was added at room temperature and followed by stirring for 6 hours. The organic layer was separated from the aqueous layer and extracted with a saturated aqueous solution of sodium bicarbonate. The combined aqueous layers were acidified with conc. hydrochloric acid and extracted with chloroform. The extract was dried over anhydrous magnesium sulfate and the solvent was removed under reduced pressure to give 1-ethoxycarbonylamino-1-carboxycyclopentane as a colorless solid.

Workup

  1. customThe organic layer was separated from the aqueous layer
  2. extractionextracted with a saturated aqueous solution of sodium bicarbonate
  3. extractionextracted with chloroform
  4. dry with materialThe extract was dried over anhydrous magnesium sulfate
  5. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-9a86c57f72b348feb9d8298d8a3ce51e
Source dataset
uspto-grants-1993_07
Patent number
US05231179

Reaction notes

Loading…