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

HRID 1463437Notes

Reaction equation

HRID 1463437 reaction equation
[CH:1](=[N:8][N:9]1[CH2:13][CH2:12][N:11]([C@@:14]2([C:32]([O:34][CH2:35][C:36]3[CH:41]=[CH:40][C:39]([N+:42]([O-:44])=[O:43])=[CH:38][CH:37]=3)=[O:33])[S:20][C@H:19]3[N:16]([C:17](=[O:31])[C@H:18]3[NH:21]C(=O)CC3C=CC=CC=3)[CH2:15]2)[C:10]1=[O:45])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C)C1C=CC=CC=1.P(Cl)(Cl)(Cl)(Cl)Cl.CO>C(Cl)Cl.O>[NH2:21][C@@H:18]1[C:17](=[O:31])[N:16]2[C@@H:19]1[S:20][C@@:14]([N:11]1[CH2:12][CH2:13][N:9]([N:8]=[CH:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[C:10]1=[O:45])([C:32]([O:34][CH2:35][C:36]1[CH:37]=[CH:38][C:39]([N+:42]([O-:44])=[O:43])=[CH:40][CH:41]=1)=[O:33])[CH2:15]2

Participants

7

Reactant 4

HCID 887MethanolHCID 949N,N-DimethylanilineHCID 24819Phosphorus pentachlorideHCID 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 54330068(3R,5R,6R)-6-amino-3-(3-benzylideneamino-2-oxo-imidazolidin-1-yl)-3-(p-nitrobenzyloxycarbonyl)-7-oxo-4-thia-1-azabicyclo[3.2.0]heptaneYield 84%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
-60 °C

Procedure

In 132 ml of methylene chloride was dissolved 6.6 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. The solution was cooled to -60° C. Thereto were added 4.66 ml of N,N-dimethylaniline and 3.3 g of phosphorus pentachloride. The mixture was stirred at -40° to -20° C. for 1 hour and cooled to -60° C. To the reaction mixture was added 13.8 ml of anhydrous methanol. The temperature of the mixture was elevated to 0° C. in 30 minutes and mixed with 66 ml of water. The resulting mixture was stirred for 15 minutes with ice cooling. The resulting crystals were collected by filtration and suspended in a mixed solvent consisting of 50 ml of water and 100 ml of methylene chloride. The suspension was adjusted to pH 7.5 with a saturated aqueous sodium hydrogencarbonate solution. The organic layer was separated and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure to obtain 4.5 g (yield: 84.0%) of (3R,5R,6R)-6-amino-3-(3-benzylideneamino-2-oxoimidazolidin-1-yl)-3-(p-nitrobenzyloxycarbonyl)-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane.

Workup

  1. temperaturecooled to -60° C
  2. waitThe temperature of the mixture was elevated to 0° C. in 30 minutes
  3. stirringThe resulting mixture was stirred for 15 minutes with ice cooling
  4. filtrationThe resulting crystals were collected by filtration
  5. customThe organic layer was separated
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-5e3cf5acccca42d3ac86952f8c272ec5
Source dataset
uspto-grants-1994_04
Patent number
US05300497

Reaction notes

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