1,1'-Carbonyldiimidazole → HCID 10599888, compound

HRID 2396670Notes

Reaction equation

HRID 2396670 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:27]=[CH:28][C:29]=1[O:30][CH3:31])[CH2:6][N:7]1[C:10](=[O:11])[C@@H:9]([NH:12][C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:14])[C@H:8]1[C@@H:23]([OH:26])[CH2:24][OH:25].[C:32](N1C=CN=C1)(N1C=CN=C1)=[O:33]>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:27]=[CH:28][C:29]=1[O:30][CH3:31])[CH2:6][N:7]1[C:10](=[O:11])[C@@H:9]([NH:12][C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:14])[C@H:8]1[C@@H:23]1[CH2:24][O:25][C:32](=[O:33])[O:26]1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 57017794HCID 57017794, compound

Product 1

HCID 10599888HCID 10599888, compoundYield 96.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

215.23 g (0.5 mol) of benzyl (2S,3S)-1-(3,4-dimethoxybenzyl)-2-[1(R),2-dihydroxyethyl]-4-oxo-3-azetidinecarbamate were dissolved In 3 l of THF at the boiling temperature. 12.61 g (0.75 mol) of 1,1'-carbonyldiimidazole were added. The mixture was boiled under reflux for 4 hours. The THF was subsequently removed by concentration, the oily residue was taken up in 1.5 l of dichloromethane, washed once with 500 ml of 1N aqueous hydrochloric acid, twice with 1 l of water each time and once with 500 ml of saturated, aqueous sodium chloride solution and dried over magnesium sulphate with the addition of about 7 g of fuller's earth. The solvent was removed by concentration. After drying there were obtained without further purification 220.3 g (yield: 96%) of pure product. M.p.: 135°-136° C.

Workup

  1. temperatureunder reflux for 4 hours
  2. customThe THF was subsequently removed by concentration
  3. washwashed once with 500 ml of 1N aqueous hydrochloric acid, twice with 1 l of water each time
  4. dry with materialonce with 500 ml of saturated, aqueous sodium chloride solution and dried over magnesium sulphate with the addition of about 7 g of fuller's earth
  5. customThe solvent was removed by concentration
  6. customAfter drying there

Sources & evidence

ORD record
ord-2ebaa0302cc44d4aaa48c79ba8385224
Source dataset
uspto-grants-1996_02
Patent number
US05494666

Reaction notes

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