Dichloromethane → (3R,5R,6R)-3-(3-amino-2-oxoimidazolidin-1-yl)-3-(p-nitrobenzyloxycarbonyl)-7-oxo-6-phenylacetamido-4-thia-1-azabicyclo[3.2.0] heptane

HRID 2081737Notes

Reaction equation

HRID 2081737 reaction equation
C(Cl)Cl.C(=[N:11][N:12]1[CH2:16][CH2:15][N:14]([C@@:17]2([C:35]([O:37][CH2:38][C:39]3[CH:44]=[CH:43][C:42]([N+:45]([O-:47])=[O:46])=[CH:41][CH:40]=3)=[O:36])[S:23][C@H:22]3[N:19]([C:20](=[O:34])[C@H:21]3[NH:24][C:25](=[O:33])[CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH2:18]2)[C:13]1=[O:48])C1C=CC=CC=1.[N+](C1C=C([N+]([O-])=O)C=CC=1NN)([O-])=O.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[NH2:11][N:12]1[CH2:16][CH2:15][N:14]([C@@:17]2([C:35]([O:37][CH2:38][C:39]3[CH:40]=[CH:41][C:42]([N+:45]([O-:47])=[O:46])=[CH:43][CH:44]=3)=[O:36])[S:23][C@H:22]3[N:19]([C:20](=[O:34])[C@H:21]3[NH:24][C:25](=[O:33])[CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH2:18]2)[C:13]1=[O:48]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 521998p-Toluenesulfonic acid monohydrateHCID 3772977(2,4-Dinitrophenyl)hydrazineHCID 54119937(3R,5R,6R)-3-(3-benzylideneamino-2-oxoimidazolidin-1-yl)-3-(p-nitrobenzyloxycarbonyl)-7-oxo-6-phenylacetamido-4-thia-1-azabicyclo[3.2.0]heptane

Product 1

HCID 18649726(3R,5R,6R)-3-(3-amino-2-oxoimidazolidin-1-yl)-3-(p-nitrobenzyloxycarbonyl)-7-oxo-6-phenylacetamido-4-thia-1-azabicyclo[3.2.0] heptaneYield 60.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a mixed solvent consisting of 30 ml of methylene chloride and 15 ml of methanol was dissolved 3.00 g of (3R,5R,6R)-3-(3-benzylideneamino-2-oxoimidazolidin-1-yl)-3-(p-nitrobenzyloxycarbonyl)-7-oxo-6-phenylacetamido-4-thia-1-azabicyclo[3.2.0]heptane. To the solution were added 1.89 g of 2,4-dinitrophenylhydrazine and 850 mg of p-toluenesulfonic acid monohydrate in this order. The mixture was stirred at room temperature for 1.5 hours. Then, the insolubles were removed by filtration. The filtrate was concentrated under reduced pressure. The residue was mixed with a mixed solvent consisting of 30 ml of methylene chloride and 7 ml of methanol. The insolubles were removed by filtration. The filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (eluant: chloroform/methanol=100/1 to 25/1) to obtain 1.56 g (yield: 60.5%) of (3R,5R,6R)-3-(3-amino-2-oxoimidazolidin-1-yl)-3-(p-nitrobenzyloxycarbonyl)-7-oxo-6-phenylacetamido-4-thia-1-azabicyclo[3.2.0] heptane.

Workup

  1. customThen, the insolubles were removed by filtration
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. additionThe residue was mixed with a mixed solvent
  4. customThe insolubles were removed by filtration
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customThe residue was purified by column chromatography (eluant: chloroform/methanol=100/1 to 25/1)

Sources & evidence

ORD record
ord-63df434f9b294ca689b043e6730134d7
Source dataset
uspto-grants-1993_02
Patent number
US05185330

Reaction notes

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