Bromhydrol → HCID 12833979, compound

HRID 1660586Notes

Reaction equation

HRID 1660586 reaction equation
[CH3:1][C:2]12[CH2:15][C:6]1([C:7]([O:9][CH2:10][C:11]([Cl:14])([Cl:13])[Cl:12])=[O:8])[N:5]1[C:16](=[O:29])[CH:17]([NH:18][C:19](=[O:28])[CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[CH:22]=3)[C@H:4]1[S:3]2.[Br-].[Al+3].[Br-].[Br-]>ClCCl>[CH3:1][CH:2]1[CH:15]=[C:6]([C:7]([O:9][CH2:10][C:11]([Cl:12])([Cl:14])[Cl:13])=[O:8])[N:5]2[C:16](=[O:29])[CH:17]([NH:18][C:19](=[O:28])[CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[CH:22]=3)[C@H:4]2[S:3]1

Participants

4

Reactant 2

HCID 166749BromhydrolHCID 70528296HCID 70528296, compound

Product 1

HCID 12833979HCID 12833979, compoundYield 85.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2,2,2-trichloroethyl 2-methyl-2,3-methylene-6-{2-(3-chlorophenyl)acetamido}penam-3-carboxylate (3.4 g.) in dried dichloromethane (50 ml.) was dropwise added at -15° C. to a solution of aluminum bromide (2.8 g.) in dried dichloromethane (20 ml.) and the mixture was stirred for 3 hours at room temperature. After the reaction, the reaction mixture was washed in turn with 5% hydrochloric acid, water, 5% sodium bicarbonate aqueous solution and water and then dried. After the solvent was distilled off, the residue was crystallized from ether to give 2,2,2-trichloroethyl 2-methyl-7-{2-(3-chlorophenyl)acetamido}-3-cephem-4-carboxylate (2.9 g.), mp 144° to 145.5° C. (dec.).

Workup

  1. customAfter the reaction
  2. washthe reaction mixture was washed in turn with 5% hydrochloric acid, water, 5% sodium bicarbonate aqueous solution and water
  3. customdried
  4. distillationAfter the solvent was distilled off
  5. customthe residue was crystallized from ether

Sources & evidence

ORD record
ord-5fce3572c3f74bf28bd43443793be3df
Source dataset
uspto-grants-1981_12
Patent number
US04308380

Reaction notes

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