Sulfuric acid magnesium salt (1:1) → Benzhydryl 7beta-(2',3'-dibromo-2'-ethylbutylideneamino)-3-(1-methyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylate

HRID 638384Notes

Reaction equation

HRID 638384 reaction equation
[NH2:1][C@@H:2]1[C:33](=[O:34])[N:4]2[C:5]([C:17]([O:19][CH:20]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[O:18])=[C:6]([CH2:9][S:10][C:11]3[N:15]([CH3:16])[N:14]=[N:13][N:12]=3)[CH2:7][S:8][C@H:3]12.[Br:35][C:36]([CH2:42][CH3:43])([CH:39]([Br:41])[CH3:40])[CH:37]=O.S([O-])([O-])(=O)=O.[Mg+2]>C(Cl)Cl>[Br:35][C:36]([CH2:42][CH3:43])([CH:39]([Br:41])[CH3:40])[CH:37]=[N:1][C@@H:2]1[C:33](=[O:34])[N:4]2[C:5]([C:17]([O:19][CH:20]([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[O:18])=[C:6]([CH2:9][S:10][C:11]3[N:15]([CH3:16])[N:14]=[N:13][N:12]=3)[CH2:7][S:8][C@H:3]12

Participants

5

Reactant 3

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 12873516(6R,7R)-Benzhydryl 7-amino-3-((1-methyl-1H-tetrazol-5-ylthio)methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylateHCID 20254158HCID 20254158, compound

Product 1

HCID 131714476Benzhydryl 7beta-(2',3'-dibromo-2'-ethylbutylideneamino)-3-(1-methyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylateYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of benzhydryl 7β-amino-3-(1-methyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylate (2.47 g, 5.00 mmol) in methylene chloride (35 ml) was added under ice-cooling a solution of 2,3-dibromo-2-ethylbutanal (1.42 g, 5.50 mmol) in methylene chloride (5 ml) followed by addition of anhydrous magnesium sulfate. The resulting mixture was stirred at room temperature for 4 hours. The reaction mixture was filtered, the filtrate was concentrated under reduced pressure and, after addition of benzene (20 ml) and thorough stirring, insolubles were filtered off. The filtrate was concentrated to dryness under reduced pressure and the reside was made powdery by the addition of ether (10 ml). The resulting powder was recovered by filtration and dried under reduced pressure to give 3.12 g (85%) of the title compound as a pale brown powder.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. additionafter addition of benzene (20 ml) and thorough stirring, insolubles
  4. filtrationwere filtered off
  5. concentrationThe filtrate was concentrated to dryness under reduced pressure
  6. additionthe reside was made powdery by the addition of ether (10 ml)
  7. filtrationThe resulting powder was recovered by filtration
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-c63c4a57aa504f428b02c59b0db21e19
Source dataset
uspto-grants-1985_12
Patent number
US04560750

Reaction notes

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