Sodium → HCID 59558623, compound

HRID 1175158Notes

Reaction equation

HRID 1175158 reaction equation
C(O[C:4]([C:6]1([C:9]2([NH:12][C:13](=[O:20])[CH2:14][C:15]([O:17][CH2:18]C)=[O:16])[CH2:11][CH2:10]2)[CH2:8][CH2:7]1)=[O:5])C.[Na]>C1(C)C=CC=CC=1.CO>[CH3:18][O:17][C:15]([CH:14]1[C:4](=[O:5])[C:6]2([CH2:7][CH2:8]2)[C:9]2([CH2:10][CH2:11]2)[NH:12][C:13]1=[O:20])=[O:16]

Participants

5

Reactant 2

HCID 5360545SodiumHCID 59558423HCID 59558423, compound

Product 1

HCID 59558623HCID 59558623, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
85 °C

Procedure

1′-(2-Ethoxycarbonyl-acetylamino)-bicyclopropyl-1-carboxylic acid ethyl ester (1 g; 3.53 mmol) in toluene (15 ml) is added rapidly to a solution of sodium (81 mg; 3.53 mmol) in methanol (3 ml) under stirring. The reaction mixture is warmed to 85° C. for 40 minutes, cooled to room temperature and the precipitate (sodium salt of title compound) filtered, washed with toluene, then heptane, dissolved in water (0.6 ml) and acidified with 2N HCl (1.75 ml). The resulting resin is decanted from water and crystallized by triturating with TBME (1 ml) to deliver the title compound as colorless crystals (633 mg; 80%).

Workup

  1. temperaturecooled to room temperature
  2. filtrationthe precipitate (sodium salt of title compound) filtered
  3. washwashed with toluene
  4. dissolutionheptane, dissolved in water (0.6 ml)
  5. customThe resulting resin is decanted from water
  6. customcrystallized
  7. customby triturating with TBME (1 ml)

Sources & evidence

ORD record
ord-572dc2d76e834493b18374892ddc17b2
Source dataset
uspto-grants-2010_11
Patent number
US07838674B2

Reaction notes

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