Toluene → Benzyl 2-Acetamido-carbapen-2-em-3-carboxylate

HRID 2231331Notes

Reaction equation

HRID 2231331 reaction equation
[NH2:1][C:2]1[CH2:3][C@@H:4]2[CH2:11][C:10](=[O:12])[N:5]2[C:6]=1[C:7]([O-:9])=[O:8].[Na+].[C:14]1([CH3:20])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[C:21](OCC)(=[O:23])[CH3:22]>>[C:21]([NH:1][C:2]1[CH2:3][C@@H:4]2[CH2:11][C:10](=[O:12])[N:5]2[C:6]=1[C:7]([O:9][CH2:20][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:8])(=[O:23])[CH3:22]

Participants

4

Reactant 3

HCID 1140TolueneHCID 8857Ethyl AcetateHCID 131715744Sodium 2-amino-carbapen-2-em-3-carboxylate

Product 1

HCID 131715758Benzyl 2-Acetamido-carbapen-2-em-3-carboxylateYield 100%

Procedure

A mixture of crystalline diazo keto ester 4 (45 mg, 0.152 mmol) rhodium octanoate (1.2 mg, 0.00154 mmol) and anhydrous toluene (3.0 ml) was heated in an oil bath at 80° and under a nitrogen atmosphere for 15 minutes. (Note: gas evolution occurred at room temperature before heating). After cooling to room temperature, the reaction mixture was diluted with ethyl acetate (3 ml), dried over magnesium sulfate, filtered, evaporated under vacuum and stripped with methylene chloride to afford 5 as a pale green oil (41 mg, 100%). Spectral data for 5:

Workup

  1. temperaturewas heated in an oil bath at 80° and under a nitrogen atmosphere for 15 minutes
  2. temperatureAfter cooling to room temperature
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated under vacuum

Sources & evidence

ORD record
ord-89a510c0c3be45949eac5899c37db31f
Source dataset
uspto-grants-1988_11
Patent number
US04782051

Reaction notes

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