Bromhydrol → HCID 70528502, compound

HRID 851579Notes

Reaction equation

HRID 851579 reaction equation
[CH3:1][C:2]12[CH2:11][C:6]1([C:7]([O:9][CH3:10])=[O:8])[N:5]1[C:12](=[O:25])[CH:13]([NH:14][C:15](=[O:24])[CH2:16][O:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C@H:4]1[S:3]2.[Br-].[Al+3].[Br-].[Br-]>ClCCl>[CH3:1][CH:2]1[CH:11]=[C:6]([C:7]([O:9][CH3:10])=[O:8])[N:5]2[C:12](=[O:25])[CH:13]([NH:14][C:15](=[O:24])[CH2:16][O:17][C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[C@H:4]2[S:3]1

Participants

4

Reactant 2

HCID 166749BromhydrolHCID 70528163HCID 70528163, compound

Product 1

HCID 70528502HCID 70528502, compoundYield 33.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of methyl 2-methyl-2,3-methylene-6-(2-phenoxyacetamido)-penam-3-carboxylate (2.1 g.) in dried dichloromethane (11 ml.) was dropwise added over 8 minutes at -10° C. to a solution of aluminum bromide (2.32 g.) in dried dichloromethane (23 ml.) and the reaction temperature was gradually elevated to room temperature, after which the mixture was stirred for 4.4 hours at room temperature. After the reaction, the reaction mixture was poured into ice-water (150 ml.) and the dichloromethane layer was separated, after which the aqueous layer was once extracted with chloroform. The combined dichloromethane and chloroform extract was washed in turn with water, 2% hydrochloric acid, water, a dilute sodium bicarbonate aqueous solution and water, and then dried over magnesium sulfate. After the solvent was distilled off, the obtained yellow oil was purified by column chromatography on silica gel (15 g.) using chloroform as developing solvent to give orange oil of methyl 2-methyl-7-(2-phenoxyacetamido)-3-cephem-4-carboxylate (0.7 g.).

Workup

  1. customwas gradually elevated to room temperature
  2. customAfter the reaction
  3. customthe dichloromethane layer was separated
  4. extractionafter which the aqueous layer was once extracted with chloroform
  5. extractionThe combined dichloromethane and chloroform extract
  6. washwas washed in turn with water, 2% hydrochloric acid, water
  7. dry with materiala dilute sodium bicarbonate aqueous solution and water, and then dried over magnesium sulfate
  8. distillationAfter the solvent was distilled off
  9. customthe obtained yellow oil was purified by column chromatography on silica gel (15 g.)

Sources & evidence

ORD record
ord-507c34d8ee2f4f39b24ac35ed9d46b78
Source dataset
uspto-grants-1983_05
Patent number
US04385176

Reaction notes

Loading…