Bromhydrol → HCID 12833969, compound

HRID 1660583Notes

Reaction equation

HRID 1660583 reaction equation
[Br-].[Al+3].[Br-].[Br-].[CH3:5][C:6]12[CH2:19][C:10]1([C:11]([O:13][CH2:14][C:15]([Cl:18])([Cl:17])[Cl:16])=[O:12])[N:9]1[C:20](=[O:31])[CH:21]([NH:22][C:23](=[O:30])[CH2:24][N:25]3[CH:29]=[N:28][N:27]=[N:26]3)[C@H:8]1[S:7]2>ClCCl>[CH3:5][CH:6]1[CH:19]=[C:10]([C:11]([O:13][CH2:14][C:15]([Cl:17])([Cl:18])[Cl:16])=[O:12])[N:9]2[C:20](=[O:31])[CH:21]([NH:22][C:23](=[O:30])[CH2:24][N:25]3[CH:29]=[N:28][N:27]=[N:26]3)[C@H:8]2[S:7]1

Participants

4

Reactant 2

HCID 166749BromhydrolHCID 15582369HCID 15582369, compound

Product 1

HCID 12833969HCID 12833969, compoundYield 52.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of aluminum bromide (0.4 g.) in dried dichloromethane (5 ml.) was dropwise added under ice-cooling to a suspension of 2,2,2-trichloroethyl 2-methyl-2,3-methylene-6-{2-(1H-tetrazol-1-yl)acetamido}penam-3-carboxylate (0.46 g.) in dried dichloromethane (10 ml.). After stirring for 4 hours at room temperature, the reaction mixture was washed in turn with 2% hydrochloric acid three times, a saturated sodium bicarbonate aqueous solution and a saturated sodium chloride aqueous solution and then dried over magnesium sulfate. After drying, the solvent was distilled off and the residue was crystallized from ethanol to give 2,2,2-trichloroethyl 2-methyl-7-{2-(1H-tetrazol-1-yl)acetamido}-3-cephem-4-caboxylate (0.24 g.), mp 168° to 170° C.

Workup

  1. washthe reaction mixture was washed in turn with 2% hydrochloric acid three times
  2. dry with materiala saturated sodium bicarbonate aqueous solution and a saturated sodium chloride aqueous solution and then dried over magnesium sulfate
  3. customAfter drying
  4. distillationthe solvent was distilled off
  5. customthe residue was crystallized from ethanol

Sources & evidence

ORD record
ord-61397c0afdcb4412a344f91f03480d70
Source dataset
uspto-grants-1981_12
Patent number
US04308380

Reaction notes

Loading…