3-Oxabicyclo(3.1.0)hexane-2,4-dione → HCID 66882748, compound

HRID 1784060Notes

Reaction equation

HRID 1784060 reaction equation
[CH:1]12[CH2:6][CH:5]1[C:4](=[O:7])[O:3][C:2]2=[O:8].[NH2:9][C:10]1[CH:15]=[CH:14][C:13]([N:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]2=[O:22])=[CH:12][C:11]=1[F:23]>C1COCC1>[F:23][C:11]1[CH:12]=[C:13]([N:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]2=[O:22])[CH:14]=[CH:15][C:10]=1[NH:9][C:4]([CH:5]1[CH2:6][CH:1]1[C:2]([OH:3])=[O:8])=[O:7]

Participants

4

Reactant 2

HCID 27347213-Oxabicyclo(3.1.0)hexane-2,4-dioneHCID 221815481-(4-Amino-3-fluorophenyl)pyridin-2-one

Product 1

HCID 66882748HCID 66882748, compoundYield 31.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-oxabicyclo[3.1.0]hexane-2,4-dione (160 mg) in THF (5 ml) was treated with 1-(4-amino-3-fluoro-phenyl)-1H-pyridin-2-one (321 mg; CAS 536747-52-1, prepared according to C. F. Bigge et al., patent application WO 2003045912). The suspension was stirred over night at r.t. The solid was collected by filtration, triturated with 1N HCl (5 ml), again collected by filtration, washed with 1N HCl, H2O, then cyclohexane and dried to give (1RS,2SR)-2-[2-fluoro-4-(2-oxo-2H-pyridin-1-yl)-phenylcarbamoyl]-cyclopropanecarboxylic acid (144 mg) as off-white solid. MS: 315.3 ([M−H]−)

Workup

  1. filtrationThe solid was collected by filtration
  2. customtriturated with 1N HCl (5 ml)
  3. filtrationagain collected by filtration
  4. washwashed with 1N HCl, H2O
  5. dry with materialcyclohexane and dried

Sources & evidence

ORD record
ord-4503bf05abfa4d1e8d80f322c67cb6b6
Source dataset
uspto-grants-2009_03
Patent number
US07501413B2

Reaction notes

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