Benzoylhydrazine → HCID 69885960, compound

HRID 1245299Notes

Reaction equation

HRID 1245299 reaction equation
C(OC([N:8]1[C:13](=[O:14])[CH:12]2[CH:10]([CH:11]2[C:15]([O-:17])=[O:16])[CH:9]1[C:18]([O-:20])=[O:19])=O)(C)(C)C.[C:21]([NH:29][NH2:30])(=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C1COCC1.[C-]#N.[K+]>[C:21]([NH:29][NH:30][C:13]([CH:12]1[CH:10]([CH:9]([C:18]([OH:20])=[O:19])[NH2:8])[CH:11]1[C:15]([OH:17])=[O:16])=[O:14])(=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 2

HCID 11955BenzoylhydrazineHCID 21911181HCID 21911181, compound

Product 1

HCID 69885960HCID 69885960, compoundYield 104.6%

Reagents, catalysts & solvents 2

HCID 9032Potassium CyanideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl (1SR, 2 SR, 5RS, 6RS) 3-tert -butoxycarbonyl-4-oxo-3-azabicyclo[3.1.0]hexane-2,6-dicarboxylate (88 mg, 0.25 mmol) in dry THF (2 mL) under argon was added benzoic hydrazide (209 mg, 1.54 mmol) and potassium cyanide (0.83 mg, 0.01 mmol). After stirring overnight in an ultrasonic bath, the solvent was removed under reduced pressure. The residue was directly purified by flash chromatography (hexane/ethyl acetate 1/1) to give 84 mg of the desired compound (72% yield).

Workup

  1. customthe solvent was removed under reduced pressure
  2. customThe residue was directly purified by flash chromatography (hexane/ethyl acetate 1/1)

Sources & evidence

ORD record
ord-d43295adf52d460a9a3e4805fbbee9a8
Source dataset
uspto-grants-2006_10
Patent number
US07125871B2

Reaction notes

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