Sodium → HCID 59558606, compound

HRID 1175160Notes

Reaction equation

HRID 1175160 reaction equation
C([O:4][C:5]([C:7]1([C:18]2([NH:21][C:22](=[O:29])[CH2:23][C:24]([O:26][CH2:27]C)=[O:25])[CH2:20][CH2:19]2)[CH2:10][N:9]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:8]1)=O)(C)C.[Na]>C1(C)C=CC=CC=1.CO>[CH3:27][O:26][C:24]([CH:23]1[C:22](=[O:29])[NH:21][C:18]2([CH2:19][CH2:20]2)[C:7]2([CH2:8][N:9]([C:11]([O:13][C:14]([CH3:16])([CH3:17])[CH3:15])=[O:12])[CH2:10]2)[C:5]1=[O:4])=[O:25]

Participants

5

Reactant 2

HCID 5360545SodiumHCID 59558365HCID 59558365, compound

Product 1

HCID 59558606HCID 59558606, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
85 °C

Procedure

The mixture of 3-[1-(2-ethoxycarbonyl-acetylamino)-cyclopropyl]-azetidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-isopropyl ester and ethyl ester (Example 180b) (350 mg; 0.35 mmol) is dissolved in toluene (5 ml) and added dropwise under stirring to a solution of sodium (20 mg; 0.85 mol) in MeOH (1 ml). The mixture is heated to 85° C. for 45 minutes, cooled, and the resulting suspension (Na-salt of title compound) filtered, washed with toluene and isopentane. The white solid is taken up in water/2N HCl (20 ml/0.5 ml) and extracted with CH2Cl2 three times. The combined organic phases are dried over Na2SO4, filtered and evaporated to dryness to deliver the title compound as almost colorless foam (166 mg; 58%).

Workup

  1. additionadded dropwise
  2. temperaturecooled
  3. filtrationthe resulting suspension (Na-salt of title compound) filtered
  4. washwashed with toluene and isopentane
  5. extractionextracted with CH2Cl2 three times
  6. dry with materialThe combined organic phases are dried over Na2SO4
  7. filtrationfiltered
  8. customevaporated to dryness

Sources & evidence

ORD record
ord-a6bdeae5ed0a44eb8a18b48ff4739cea
Source dataset
uspto-grants-2010_11
Patent number
US07838674B2

Reaction notes

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