Triethylamine → HCID 86740485, compound

HRID 621155Notes

Reaction equation

HRID 621155 reaction equation
[C:1]1(=[O:24])[N:5]([C@H:6]2[C@@H:9](/[CH:10]=[CH:11]/[C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[NH:8][C:7]2=[O:18])[C:4](=[O:19])[C:3]2=[CH:20][CH:21]=[CH:22][CH:23]=[C:2]12.C(N(CC)CC)C.[Si:32](Cl)([C:35]([CH3:38])([CH3:37])[CH3:36])([CH3:34])[CH3:33]>CN(C)C=O.C(OCC)(=O)C.O>[C:4]1(=[O:19])[N:5]([C@H:6]2[C@@H:9](/[CH:10]=[CH:11]/[C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[N:8]([Si:32]([C:35]([CH3:38])([CH3:37])[CH3:36])([CH3:34])[CH3:33])[C:7]2=[O:18])[C:1](=[O:24])[C:2]2=[CH:23][CH:22]=[CH:21][CH:20]=[C:3]12

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 86740484HCID 86740484, compound

Product 1

HCID 86740485HCID 86740485, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

In 6 ml of N,N-dimethylformamide is dissolved 546 mg of cis-3-phthalimido-4-(E)-styryl-2-oxoazetidine and under ice-cooling and stirring, 0.36 ml of triethylamine and 323 mg of tert-butyldimethylsilyl chloride are added. The mixture is stirred for 30 minutes and further stirred at room temperature for 4 hours and, then, the reaction mixture is shaken with ethyl acetate and water. The ethyl acetate layer is taken, washed twice with water and once with saturated aqueous sodium chloride in this order and dried over anhydrous sodium sulfate. It is concentrated under reduced pressure and the residue is purified by silica gel column chromatography (eluent: chloroform) and crystallized from ether to give cis-3-phthalimido-4-(E)-styryl-1-(tertbutyldimethylsilyl)-2-oxoazetidine, melting at 167°-168° C.

Workup

  1. temperatureunder ice-cooling
  2. stirringThe mixture is stirred for 30 minutes
  3. stirringfurther stirred at room temperature for 4 hours
  4. washwashed twice with water and once with saturated aqueous sodium chloride in this order
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationIt is concentrated under reduced pressure
  7. customthe residue is purified by silica gel column chromatography (eluent: chloroform)
  8. customcrystallized from ether

Sources & evidence

ORD record
ord-86849ee96ae1418d891d1cf9edd3502b
Source dataset
uspto-grants-1989_04
Patent number
US04822788

Reaction notes

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