Sodium → HCID 59558650, compound

HRID 1175155Notes

Reaction equation

HRID 1175155 reaction equation
[Na].CO[C:4]([C:6]1([CH2:17][NH:18][C:19](=[O:26])[CH2:20][C:21]([O:23][CH2:24]C)=[O:22])[CH2:9][N:8]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:7]1)=[O:5]>CO.C1(C)C=CC=CC=1>[CH3:24][O:23][C:21]([CH:20]1[C:4](=[O:5])[C:6]2([CH2:9][N:8]([C:10]([O:12][C:13]([CH3:14])([CH3:15])[CH3:16])=[O:11])[CH2:7]2)[CH2:17][NH:18][C:19]1=[O:26])=[O:22]

Participants

5

Reactant 2

HCID 5360545SodiumHCID 59558653HCID 59558653, compound

Product 1

HCID 59558650HCID 59558650, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

Sodium metal (870 mg; 38 mmol) is dissolved in methanol (55 ml) and combined with a solution of 3-[(2-ethoxycarbonyl-acetylamino)-methyl]-azetidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-methyl ester in toluene (165 ml). The reaction mixture is heated to 90° C. for 1 hour, cooled to 7-9° C. and the precipitated white crystals (Na-salt of title compound) filtered off. The crystals are dissolved in water, acidified by the addition of 2N HCl and extracted with CH2Cl2 three times. The combined organic phases are dried over Na2SO4, filtered, evaporated and yield the title compound as white crystals (5.6 g; 48%). A second crop of the title compound is obtained by evaporating the above toluene/methanol filtrate to almost dryness, taking up the resin in 2N HCl and extracting with CH2Cl2 three times. The combined organic phases are dried over Na2SO4, filtered, evaporated and yielded the second crop of title compound as brownish solid (3.22 g; 27%).

Workup

  1. temperaturecooled to 7-9° C.
  2. filtrationthe precipitated white crystals (Na-salt of title compound) filtered off
  3. dissolutionThe crystals are dissolved in water
  4. additionacidified by the addition of 2N HCl
  5. extractionextracted with CH2Cl2 three times
  6. dry with materialThe combined organic phases are dried over Na2SO4
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-894021dc7ff44eb482b4fe964441c6a3
Source dataset
uspto-grants-2010_11
Patent number
US07838674B2

Reaction notes

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