Potassium Hydroxide → 2-(cis-4-Tert-butoxycarbonylamino-cyclopent-2-enylmethyl)-malonic acid monoethyl ester

HRID 1789900Notes

Reaction equation

HRID 1789900 reaction equation
[OH-].[K+].[CH2:3]([O:5][C:6](=[O:27])[CH:7]([CH2:13][C@H:14]1[CH2:18][C@@H:17]([NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH:16]=[CH:15]1)[C:8]([O:10]CC)=[O:9])[CH3:4]>C(O)C.[Cl-].[Na+].O>[CH2:3]([O:5][C:6](=[O:27])[CH:7]([CH2:13][C@H:14]1[CH2:18][C@@H:17]([NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH:16]=[CH:15]1)[C:8]([OH:10])=[O:9])[CH3:4]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 696502402-(Cis-4-tert-butoxycarbonylamino-cyclopent-2-enylmethyl)-malonic acid diethyl ester

Product 1

HCID 696503392-(cis-4-Tert-butoxycarbonylamino-cyclopent-2-enylmethyl)-malonic acid monoethyl esterYield 82.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of KOH (0.19 g; 3.4 mmol) in ethanol (6 mL) was added to a solution of 2-(Cis-4-tert-butoxycarbonylamino-cyclopent-2-enylmethyl)-malonic acid diethyl ester (1.15 g; 3.2 mmol) in ethanol (6 mL) at 0° C. The reaction mixture was stirred at room temperature overnight, concentrated and ice-water (400 mL) was added. The aqueous phase was washed with diethyl ether (the emulsion formed during the extraction was treated with brine in order to get good phase separation), acidified to pH 3 with 0.5 M HCl, and extracted with diethyl ether. The organic phase was dried and concentrated under reduced pressure to afford 2-(cis4-tert-butoxycarbonylamino-cyclopent-2-enylmethyl)-malonic acid monoethyl ester (0.86 g, 81%) as white crystals.

Workup

  1. concentrationconcentrated
  2. additionice-water (400 mL) was added
  3. washThe aqueous phase was washed with diethyl ether (the emulsion
  4. customformed during the extraction
  5. customto get good
  6. customphase separation),
  7. extractionextracted with diethyl ether
  8. customThe organic phase was dried
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-63e0465be5124fb2b74f57b8ac4c8fcc
Source dataset
uspto-grants-2006_07
Patent number
US07071175B1

Reaction notes

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