3,5-Di-tert-butyl-4-hydroxybenzaldehyde → (3R,5R,6R)-3-(3-benzylideneamino-2-oxoimidazolidin-1-yl)-6-(3,5-di-tert-butyl-4-hydroxybenzylideneamino)-3-(p-nitrobenzyloxycarbonyl)-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane

HRID 2081743Notes

Reaction equation

HRID 2081743 reaction equation
[NH2:1][C@@H:2]1[C:8](=[O:9])[N:7]2[C@@H:3]1[S:4][C@@:5]([N:23]1[CH2:27][CH2:26][N:25]([N:28]=[CH:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:24]1=[O:36])([C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=1)=[O:11])[CH2:6]2.[C:37]([C:41]1[CH:42]=[C:43]([CH:46]=[C:47]([C:50]([CH3:53])([CH3:52])[CH3:51])[C:48]=1[OH:49])[CH:44]=O)([CH3:40])([CH3:39])[CH3:38]>C1C=CC=CC=1>[CH:29](=[N:28][N:25]1[CH2:26][CH2:27][N:23]([C@@:5]2([C:10]([O:12][CH2:13][C:14]3[CH:15]=[CH:16][C:17]([N+:20]([O-:22])=[O:21])=[CH:18][CH:19]=3)=[O:11])[S:4][C@H:3]3[N:7]([C:8](=[O:9])[C@H:2]3[N:1]=[CH:44][C:43]3[CH:42]=[C:41]([C:37]([CH3:38])([CH3:40])[CH3:39])[C:48]([OH:49])=[C:47]([C:50]([CH3:53])([CH3:52])[CH3:51])[CH:46]=3)[CH2:6]2)[C:24]1=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

4

Reactant 2

HCID 732193,5-Di-tert-butyl-4-hydroxybenzaldehydeHCID 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]heptane

Product 1

HCID 135979311(3R,5R,6R)-3-(3-benzylideneamino-2-oxoimidazolidin-1-yl)-6-(3,5-di-tert-butyl-4-hydroxybenzylideneamino)-3-(p-nitrobenzyloxycarbonyl)-7-oxo-4-thia-1-azabicyclo[3.2.0]heptaneYield 98.6%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

30 ml of benzene was added to 1.00 g of (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 and 0.46 g of 3,5-di-tert-butyl-4-hydroxybenzaldehyde. The mixture was subjected to azeotropy and dehydration under reflux for 1 hour using a Dean-Stark aparatus. The reaction mixture was cooled, and the solvent was removed by distillation under reduced pressure to obtain 1.40 g (yield: 98.6%) of (3R,5R,6R)-3-(3-benzylideneamino-2-oxoimidazolidin-1-yl)-6-(3,5-di-tert-butyl-4-hydroxybenzylideneamino)-3-(p-nitrobenzyloxycarbonyl)-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane.

Workup

  1. temperatureunder reflux for 1 hour
  2. temperatureThe reaction mixture was cooled
  3. customthe solvent was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-2f3c9e9c45ee4e8b815114e1bc0c6331
Source dataset
uspto-grants-1993_02
Patent number
US05185330

Reaction notes

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