Dichloromethane → 2,2,2-Trichloroethyl 2-methyl-7-(3-oxo-4-bromobutyramido)-3-cephem-4-carboxylate

HRID 261842Notes

Reaction equation

HRID 261842 reaction equation
Cl.[CH3:2][CH:3]1[CH:8]=[C:7]([C:9]([O:11][CH2:12][C:13]([Cl:16])([Cl:15])[Cl:14])=[O:10])[N:6]2[C:17](=[O:20])[CH:18]([NH2:19])[C@H:5]2[S:4]1.C[Si](CC(N)=O)(C)C.C(Cl)Cl.[O:32]=[C:33]([CH2:38][Br:39])[CH2:34][C:35](Br)=[O:36]>C(Cl)(Cl)(Cl)Cl.O>[CH3:2][CH:3]1[CH:8]=[C:7]([C:9]([O:11][CH2:12][C:13]([Cl:16])([Cl:14])[Cl:15])=[O:10])[N:6]2[C:17](=[O:20])[CH:18]([NH:19][C:35](=[O:36])[CH2:34][C:33](=[O:32])[CH2:38][Br:39])[C@H:5]2[S:4]1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 357676Acetamide, 2-(trimethylsilyl)-HCID 128310484-Bromo-3-oxobutanoyl bromideHCID 128341352,2,2-Trichloroethyl 2-methyl-7-amino-3-cephem-4-carboxylate hydrochloride

Product 1

HCID 1317114902,2,2-Trichloroethyl 2-methyl-7-(3-oxo-4-bromobutyramido)-3-cephem-4-carboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 2,2,2-trichloroethyl 2-methyl-7-amino-3-cephem-4-carboxylate hydrochloride (0.38 g.), trimethylsilylacetamide (1.1 g.) and methylene chloride (10 ml.) was stirred for 30 minutes at room temperature, and thus obtained solution was cooled to -15° C. To the solution was added dropwise 3-oxo-4-bromobutyryl bromide (1.0 m mole) in carbon tetrachloride (13 ml.) under cooling to -15° C., and the mixture was stirred for 1.5 hours at the same temperature and for 30 minutes without external cooling. The mixture was poured into cold water, and then the organic layer was separated therefrom. The organic layer was washed with 2N hydrochloric acid (8 ml ×3) and water (10 ml ×2) in turn, dried over magnesium sulfate and then filtered. The filtrate was concentrated under reduced pressure. The residue was pulverized in diisopropyl ether, collected by filtration and then dried to give pale brown powder of 2,2,2-trichloroethyl 2-methyl-7-(3-oxo-4-bromobutyramido)-3-cephem-4-carboxylate (0.31 g.), mp 78° to 83° C. (dec.).

Workup

  1. temperaturethus obtained solution was cooled to -15° C
  2. temperatureunder cooling to -15° C.
  3. stirringthe mixture was stirred for 1.5 hours at the same temperature and for 30 minutes without external cooling
  4. customthe organic layer was separated
  5. washThe organic layer was washed with 2N hydrochloric acid (8 ml ×3) and water (10 ml ×2) in turn
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated under reduced pressure
  9. filtrationcollected by filtration
  10. customdried

Sources & evidence

ORD record
ord-7d60be4214084bcea0b29baf97ebdeff
Source dataset
uspto-grants-1979_05
Patent number
US04152433

Reaction notes

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