Sodium Chloride → HCID 13174771, compound

HRID 2109355Notes

Reaction equation

HRID 2109355 reaction equation
[C:1]1([CH:7]([O:14][C:15]([CH:17]2[N:21]3[C:22](=[O:26])[C:23](Br)(Br)[C@H:20]3[S:19](=[O:27])[C:18]2([CH3:29])[CH3:28])=[O:16])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Bi].[Cl-].[Na+].[Al]>ClCCl.CO>[C:1]1([CH:7]([O:14][C:15]([CH:17]2[N:21]3[C:22](=[O:26])[CH2:23][C@H:20]3[S:19](=[O:27])[C:18]2([CH3:29])[CH3:28])=[O:16])[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 5359268AluminumHCID 5359367BismuthHCID 14096412HCID 14096412, compound3×

Product 1

HCID 13174771HCID 13174771, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
22.5 °C

Procedure

A 86.6 g quantity of 6,6-dibromo-2,2-dimethylpenam-3-carboxylic acid 1-oxide diphenylmethyl ester (Compound 1) [compound of the formula (1) wherein X═Y═Br, R=diphenylmethyl, n=1] was dissolved in 300 mL of dichloromethane. To the solution was added 36 mL of methanol with stirring and then added a suspension of 1.05 g of metal bismuth in 112 mL of 20% aqueous solution of sodium chloride. While maintaining at 20 to 25° C., to the mixture was added 10 g of aluminum powder, each 1 g, at intervals of 10 minutes, thereafter the mixture was refluxed with heating. After 23.5 hours, the reaction mixture was cooled to room temperature, an organic layer was separated and washed with diluted hydrochloric acid and 5% aqueous solution of sodium chloride. The organic layer was concentrated to give 2,2-dimethylpenam-3-carboxylic acid 1-oxide diphenylmethyl ester (Compound 2) [compound of the formula (2) wherein R=diphenylmethyl, n=1].

Workup

  1. additionadded
  2. temperatureeach 1 g, at intervals of 10 minutes, thereafter the mixture was refluxed
  3. temperaturewith heating
  4. temperaturethe reaction mixture was cooled to room temperature
  5. customan organic layer was separated
  6. washwashed with diluted hydrochloric acid and 5% aqueous solution of sodium chloride
  7. concentrationThe organic layer was concentrated

Sources & evidence

ORD record
ord-34e8bbf76a3d4992877a8265a3b2797f
Source dataset
uspto-grants-2009_04
Patent number
US07514553B2

Reaction notes

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