Pyridine → methyl (1aRS,7bSR)-5-(4-fluoro-2-nitrobenzenesulfonylamino)-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylate

HRID 927992Notes

Reaction equation

HRID 927992 reaction equation
[NH2:1][C:2]1[C:11]([C:12]([O:14][CH3:15])=[O:13])=[C:10]2[C:5]([CH:6]3[CH2:16][CH:7]3[CH2:8][O:9]2)=[CH:4][CH:3]=1.[F:17][C:18]1[CH:23]=[CH:22][C:21]([S:24](Cl)(=[O:26])=[O:25])=[C:20]([N+:28]([O-:30])=[O:29])[CH:19]=1.N1C=CC=CC=1>C(Cl)Cl>[F:17][C:18]1[CH:23]=[CH:22][C:21]([S:24]([NH:1][C:2]2[C:11]([C:12]([O:14][CH3:15])=[O:13])=[C:10]3[C:5]([CH:6]4[CH2:16][CH:7]4[CH2:8][O:9]3)=[CH:4][CH:3]=2)(=[O:26])=[O:25])=[C:20]([N+:28]([O-:30])=[O:29])[CH:19]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 27590464-Fluoro-2-nitrobenzene-1-sulfonyl chlorideHCID 86713293Methyl 5-amino-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylate2×

Product 1

HCID 86713325methyl (1aRS,7bSR)-5-(4-fluoro-2-nitrobenzenesulfonylamino)-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylateYield 57.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of methyl (1aRS,7bSR)-5-amino-1,1a,2,7b-tetrahydrocyclopropa-[c]chromene-4-carboxylate (Intermediate 42, 0.1 g), 4-fluoro-2-nitrobenzenesulfonyl chloride (0.115 g) and pyridine (2 mL) in DCM (5 mL) was stirred at room temperature overnight. The mixture was concentrated under vacuum and the residue was partitioned between ethyl acetate and water. The organic layer was dried (Na2SO4) and filtered and the filtrate was evaporated to dryness. The residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and petroleum ether (20%) to give methyl (1aRS,7bSR)-5-(4-fluoro-2-nitrobenzenesulfonylamino)-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylate (0.11 g) as a yellow oil.

Workup

  1. concentrationThe mixture was concentrated under vacuum
  2. customthe residue was partitioned between ethyl acetate and water
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. filtrationfiltered
  5. customthe filtrate was evaporated to dryness
  6. customThe residue was purified by chromatography on silica
  7. washeluting with a mixture of ethyl acetate and petroleum ether (20%)

Sources & evidence

ORD record
ord-496fb99a84044b1e8924143a7f6243a2
Source dataset
uspto-grants-2016_03
Patent number
US09290472B2

Reaction notes

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