Triethylamine → HCID 70559499, compound

HRID 2052095Notes

Reaction equation

HRID 2052095 reaction equation
C(N(CC)CC)C.[Br:8]N1C(=O)CCC1=O.[C:16]([NH:24][CH:25]1[C:41](=[O:42])[N:27]2[C:28]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])=[C:29]([CH3:33])[CH2:30][S:31](=[O:32])[C@H:26]12)(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C(Cl)Cl.[W]>[C:16]([NH:24][CH:25]1[C:41](=[O:42])[N:27]2[C:28]([C:34]([O:36][C:37]([CH3:38])([CH3:40])[CH3:39])=[O:35])=[C:29]([CH3:33])[CH:30]([Br:8])[S:31](=[O:32])[C@H:26]12)(=[O:23])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 67184N-bromobutanimideHCID 70464442t-Butyl 7-benzamido-3-methyl-3-cephem-4-carboxylate 1-oxide

Product 1

HCID 70559499HCID 70559499, compoundYield 112.9%

Reagents, catalysts & solvents 2

HCID 23964TungstenCatalystHCID 6344DichloromethaneSolvent

Procedure

4.2 ml (30 mmoles) of triethylamine and 3.28 g (24 mmoles) of N-bromosuccinimide were sequentially added to a solution of 7.8 g (20 mmoles) of t-butyl 7-benzamido-3-methyl-3-cephem-4-carboxylate 1-oxide in 150 ml of methylene chloride under nitrogen and cooled in an ice bath and the mixture was irradiated with a 150 W tungsten lamp for 15 minutes. The dark-brown reaction mixture was washed with a dilute hydrochloric acid solution (pH 1) and then twice with 250 ml portions of water. The organic layer was dried over magnesium sulfate, filtered and evaporated to dryness to obtain 10.6 g (70% yield-purity 62%) of t-butyl 7-benzamido-2-bromo-3-methyl-3-cephem-4-carboxylate 1-oxide.

Workup

  1. temperaturecooled in an ice bath
  2. washThe dark-brown reaction mixture was washed with a dilute hydrochloric acid solution (pH 1)
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-172a2682708944fbb0ea44b360c7bd74
Source dataset
uspto-grants-1980_01
Patent number
US04182870

Reaction notes

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