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

HRID 1762679Notes

Reaction equation

HRID 1762679 reaction equation
O[C@@H]([C@@H:4]1[C@@H:7]([C@@H:8](C)[C:9](=O)[C:10](=[N+]=[N-])[C:11]([O:13][CH2:14][CH:15]=[CH2:16])=[O:12])[NH:6][C:5]1=[O:21])C.[C:22]1([CH3:28])[CH:27]=[CH:26]C=CC=1>C(OCC)(=O)C>[C:5]([NH:6][C:9]1[CH2:8][C@@H:7]2[CH2:4][C:5](=[O:21])[N:6]2[C:10]=1[C:11]([O:13][CH2:14][C:15]1[CH:16]=[CH:26][CH:27]=[CH:22][CH:28]=1)=[O:12])(=[O:21])[CH3:4]

Participants

4

Reactant 2

HCID 1140TolueneHCID 54331596(3S,4R)-3-[(R)-1-hydroxyethyl]-4-[(R)-1-methyl-3-diazo-3-allyloxycarbonyl-2-oxopropyl]-2-azetidinone

Product 1

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

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

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%).

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-c5e4a8adafb240338ce746c2887ebb87
Source dataset
uspto-grants-1989_05
Patent number
US04833167

Reaction notes

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