1,3-Dibromo-5,5-dimethylhydantoin → HCID 70463777, compound

HRID 1902924Notes

Reaction equation

HRID 1902924 reaction equation
[CH3:1][C:2]1[CH2:3][S:4](=[O:24])[C@@H:5]2[CH:12]([NH:13][C:14](=[O:22])[CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:11](=[O:23])[N:6]2[C:7]=1[C:8]([OH:10])=[O:9].[CH3:25][Si:26]([CH3:35])([CH3:34])NC(=O)C(Cl)(Cl)Cl.[Br:36]N1C(C)(C)C(=O)N(Br)C1=O>ClCCCl>[Br:36][CH2:1][C:2]1[CH2:3][S:4](=[O:24])[C@@H:5]2[CH:12]([NH:13][C:14](=[O:22])[CH2:15][C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:11](=[O:23])[N:6]2[C:7]=1[C:8]([O:10][Si:26]([CH3:35])([CH3:34])[CH3:25])=[O:9]

Participants

5

Reactant 3

HCID 64791,3-Dibromo-5,5-dimethylhydantoinHCID 20491060N-trimethylsilyl-trichloroacetamideHCID 70485748HCID 70485748, compound

Product 1

HCID 70463777HCID 70463777, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

420 mg (1.21 mmoles) of 3-methyl-7-phenylacetamido-3-cephem-4-carboxylic acid-1-oxide were silylated by stirring at 30° C. for 1.5 hours in 60 ml of 1,2-dichloroethane with 1.0 g (4.3 mmoles) of N-trimethylsilyltrichloroacetamide. The slightly yellow, substantially clear solution obtained was cooled in an ice-bath and bromination was carried out in 15 minutes using 250 mg (0.87 mmole) of 1,3-dibromo-5,5-dimethylhydantoin as the brominating agent. During the bromination reaction, the mixture was irradiated with a 520 W fluorescent lamp to obtain a 48% yield of trimethylsilyl 3-bromomethyl-7-phenylacetamido-3-cephem-4-carboxylate-1-oxide.

Workup

  1. customThe slightly yellow, substantially clear solution obtained
  2. temperaturewas cooled in an ice-bath
  3. customDuring the bromination reaction
  4. customthe mixture was irradiated with a 520 W fluorescent lamp

Sources & evidence

ORD record
ord-c3255a04bd584e159541c8c509a1441b
Source dataset
uspto-grants-1982_12
Patent number
US04366315

Reaction notes

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