m-Anisohydrazide → HCID 69886167, compound

HRID 1245304Notes

Reaction equation

HRID 1245304 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.[CH3:21][O:22][C:23]1[CH:24]=[C:25]([CH:30]=[CH:31][CH:32]=1)[C:26]([NH:28][NH2:29])=[O:27]>C1COCC1.[C-]#N.[K+]>[C:15]([CH:11]1[CH:12]([C:13]([NH:29][NH:28][C:26](=[O:27])[C:25]2[CH:30]=[CH:31][CH:32]=[C:23]([O:22][CH3:21])[CH:24]=2)=[O:14])[CH:10]1[CH:9]([C:18]([OH:20])=[O:19])[NH2:8])([OH:17])=[O:16]

Participants

5

Reactant 2

HCID 79848m-AnisohydrazideHCID 21911181HCID 21911181, compound

Product 1

HCID 69886167HCID 69886167, compoundYield 133.3%

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 (150 mg, 0.44 mmol) in dry THF (3 mL) under argon was added 3-methoxybenzoic hydrazide (438 mg, 2.64 mmol) and potassium cyanide (1.43 mg, 0.02 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 206 mg of the desired compound (92% 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-4fcb30491ffe4e0b9363696c63fed1da
Source dataset
uspto-grants-2006_10
Patent number
US07125871B2

Reaction notes

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